Synthetic Routes to, Transformations of, and Rather Surprising Stabilities of (N-Methyl-N-phenylcarbamoyl) sulfenyl Chloride,((N-Methyl-N-phenylcarbamoyl) dithio) …

AM Schrader, AL Schroll, G Barany

Index: Schrader, Alex M.; Schroll, Alayne L.; Barany, George Journal of Organic Chemistry, 2011 , vol. 76, # 19 p. 7882 - 7892

Full Text: HTML

Citation Number: 5

Abstract

The title compound classes,(carbamoyl) sulfenyl chlorides and ((carbamoyl) dithio) carbonyl chlorides, have been implicated previously as unstable, albeit trappable, intermediates in organosulfur chemistry. The present work reports for each of these functional groups:(i) several routes to prepare it in the N-methylaniline family;(ii) its direct structural characterization by several spectroscopic techniques;(iii) its rather unexpected stability ...

 Related Synthetic Route
S-(N-methylanilino) N-methyl-N-phenylcarbamothioate Structure

87463-10-3

S-(N-methylanil...

~0%

3-METHYL-2(3H)-BENZOTHIAZOLONE Structure

2786-62-1

3-METHYL-2(3H)-...

N-methylaniline,hydrochloride Structure

2739-12-0

N-methylaniline...

(trichloromethyl)(N-methyl-N-phenylcarbamoyl)disulfane Structure

87462-99-5

(trichloromethy...

~%

3-METHYL-2(3H)-BENZOTHIAZOLONE Structure

2786-62-1

3-METHYL-2(3H)-...

O-isopropyl N-methyl-N-phenylthiocarbamate Structure

100244-42-6

O-isopropyl N-m...

~%

3-METHYL-2(3H)-BENZOTHIAZOLONE Structure

2786-62-1

3-METHYL-2(3H)-...

carbaniloyl chloride, n-methyl- Structure

4285-42-1

carbaniloyl chl...

O-methyl N-methyl-N-phenylcarbamothioate Structure

87463-11-4

O-methyl N-meth...

~%

3-METHYL-2(3H)-BENZOTHIAZOLONE Structure

2786-62-1

3-METHYL-2(3H)-...

carbaniloyl chloride, n-methyl- Structure

4285-42-1

carbaniloyl chl...

O-ethyl N-methyl-N-phenylthiocarbamate Structure

87463-00-1

O-ethyl N-methy...

~%

3-METHYL-2(3H)-BENZOTHIAZOLONE Structure

2786-62-1

3-METHYL-2(3H)-...

carbaniloyl chloride, n-methyl- Structure

4285-42-1

carbaniloyl chl...

O-ethyl N-methyl-N-phenylthiocarbamate Structure

87463-00-1

O-ethyl N-methy...

~%

3-METHYL-2(3H)-BENZOTHIAZOLONE Structure

2786-62-1

3-METHYL-2(3H)-...

(N-methyl-N-phenylcarbamoyl)sulfenyl chloride Structure

100244-53-9

(N-methyl-N-phe...

Bis(N-methyl-N-phenylcarbamoyl)disulfane Structure

51480-12-7

Bis(N-methyl-N-...

~%

3-METHYL-2(3H)-BENZOTHIAZOLONE Structure

2786-62-1

3-METHYL-2(3H)-...

carbaniloyl chloride, n-methyl- Structure

4285-42-1

carbaniloyl chl...

N-methyl-N-trimethylsilylaniline Structure

17890-34-5

N-methyl-N-trim...

~%

3-METHYL-2(3H)-BENZOTHIAZOLONE Structure

2786-62-1

3-METHYL-2(3H)-...

O-methyl N-methyl-N-phenylcarbamothioate Structure

87463-11-4

O-methyl N-meth...

~%

3-METHYL-2(3H)-BENZOTHIAZOLONE Structure

2786-62-1

3-METHYL-2(3H)-...

S-(N-methylanilino) N-methyl-N-phenylcarbamothioate Structure

87463-10-3

S-(N-methylanil...

~%

3-METHYL-2(3H)-BENZOTHIAZOLONE Structure

2786-62-1

3-METHYL-2(3H)-...

N-methylaniline,hydrochloride Structure

2739-12-0

N-methylaniline...

(N-methyl-N-phenylcarbamoyl)sulfenyl chloride Structure

100244-53-9

(N-methyl-N-phe...

O-isopropyl N-methyl-N-phenylthiocarbamate Structure

100244-42-6

O-isopropyl N-m...

~%

3-METHYL-2(3H)-BENZOTHIAZOLONE Structure

2786-62-1

3-METHYL-2(3H)-...

carbaniloyl chloride, n-methyl- Structure

4285-42-1

carbaniloyl chl...

(N-methyl-N-phenylcarbamoyl)sulfenyl chloride Structure

100244-53-9

(N-methyl-N-phe...

N-Methylaniline Structure

100-61-8

N-Methylaniline

~%

3-METHYL-2(3H)-BENZOTHIAZOLONE Structure

2786-62-1

3-METHYL-2(3H)-...

carbaniloyl chloride, n-methyl- Structure

4285-42-1

carbaniloyl chl...

O-isopropyl N-methyl-N-phenylthiocarbamate Structure

100244-42-6

O-isopropyl N-m...

~%

3-METHYL-2(3H)-BENZOTHIAZOLONE Structure

2786-62-1

3-METHYL-2(3H)-...

O-isopropyl N-methyl-N-phenylthiocarbamate Structure

100244-42-6

O-isopropyl N-m...

N-Methylaniline Structure

100-61-8

N-Methylaniline

~%

3-METHYL-2(3H)-BENZOTHIAZOLONE Structure

2786-62-1

3-METHYL-2(3H)-...

carbaniloyl chloride, n-methyl- Structure

4285-42-1

carbaniloyl chl...

Detail
N-methyl-N-trimethylsilylaniline Structure

17890-34-5

N-methyl-N-trim...

~%

3-METHYL-2(3H)-BENZOTHIAZOLONE Structure

2786-62-1

3-METHYL-2(3H)-...

carbaniloyl chloride, n-methyl- Structure

4285-42-1

carbaniloyl chl...

N-methyl-N-trimethylsilylaniline Structure

17890-34-5

N-methyl-N-trim...

Chloro(chlorosulfanyl)oxomethane Structure

2757-23-5

Chloro(chlorosu...

~%

3-METHYL-2(3H)-BENZOTHIAZOLONE Structure

2786-62-1

3-METHYL-2(3H)-...

O-methyl N-methyl-N-phenylcarbamothioate Structure

87463-11-4

O-methyl N-meth...

Chloro(chlorosulfanyl)oxomethane Structure

2757-23-5

Chloro(chlorosu...

~%

3-METHYL-2(3H)-BENZOTHIAZOLONE Structure

2786-62-1

3-METHYL-2(3H)-...

((N-methyl-N-phenylcarbamoyl)dithio)carbonyl chloride Structure

100244-48-2

((N-methyl-N-ph...

O-ethyl N-methyl-N-phenylthiocarbamate Structure

87463-00-1

O-ethyl N-methy...

Chloro(chlorosulfanyl)oxomethane Structure

2757-23-5

Chloro(chlorosu...

~%

3-METHYL-2(3H)-BENZOTHIAZOLONE Structure

2786-62-1

3-METHYL-2(3H)-...

((N-methyl-N-phenylcarbamoyl)dithio)carbonyl chloride Structure

100244-48-2

((N-methyl-N-ph...

O-isopropyl N-methyl-N-phenylthiocarbamate Structure

100244-42-6

O-isopropyl N-m...

Chloro(chlorosulfanyl)oxomethane Structure

2757-23-5

Chloro(chlorosu...

~%

3-METHYL-2(3H)-BENZOTHIAZOLONE Structure

2786-62-1

3-METHYL-2(3H)-...

((N-methyl-N-phenylcarbamoyl)dithio)carbonyl chloride Structure

100244-48-2

((N-methyl-N-ph...

Chloro(chlorosulfanyl)oxomethane Structure

2757-23-5

Chloro(chlorosu...

N-Methylaniline Structure

100-61-8

N-Methylaniline

~%

3-METHYL-2(3H)-BENZOTHIAZOLONE Structure

2786-62-1

3-METHYL-2(3H)-...

(N-methyl-N-phenylcarbamoyl)sulfenyl chloride Structure

100244-53-9

(N-methyl-N-phe...

O-methyl N-methyl-N-phenylcarbamothioate Structure

87463-11-4

O-methyl N-meth...

Chloro(chlorosulfanyl)oxomethane Structure

2757-23-5

Chloro(chlorosu...

N-Methylaniline Structure

100-61-8

N-Methylaniline

~%

3-METHYL-2(3H)-BENZOTHIAZOLONE Structure

2786-62-1

3-METHYL-2(3H)-...

Detail
O-methyl N-methyl-N-phenylcarbamothioate Structure

87463-11-4

O-methyl N-meth...

N-Methylaniline Structure

100-61-8

N-Methylaniline

~92%

S-(N-methylanilino) N-methyl-N-phenylcarbamothioate Structure

87463-10-3

S-(N-methylanil...

O-ethyl N-methyl-N-phenylthiocarbamate Structure

87463-00-1

O-ethyl N-methy...

N-Methylaniline Structure

100-61-8

N-Methylaniline

~84%

S-(N-methylanilino) N-methyl-N-phenylcarbamothioate Structure

87463-10-3

S-(N-methylanil...

N-methyl-N-trimethylsilylaniline Structure

17890-34-5

N-methyl-N-trim...

Chloro(chlorosulfanyl)oxomethane Structure

2757-23-5

Chloro(chlorosu...

~93%

S-(N-methylanilino) N-methyl-N-phenylcarbamothioate Structure

87463-10-3

S-(N-methylanil...

O-isopropyl N-methyl-N-phenylthiocarbamate Structure

100244-42-6

O-isopropyl N-m...

N-Methylaniline Structure

100-61-8

N-Methylaniline

~%

3-METHYL-2(3H)-BENZOTHIAZOLONE Structure

2786-62-1

3-METHYL-2(3H)-...

carbaniloyl chloride, n-methyl- Structure

4285-42-1

carbaniloyl chl...

Detail
N-methyl-N-trimethylsilylaniline Structure

17890-34-5

N-methyl-N-trim...

Chloro(chlorosulfanyl)oxomethane Structure

2757-23-5

Chloro(chlorosu...

~93%

S-(N-methylanilino) N-methyl-N-phenylcarbamothioate Structure

87463-10-3

S-(N-methylanil...

(N-methyl-N-phenylcarbamoyl)sulfenyl chloride Structure

100244-53-9

(N-methyl-N-phe...

O-methyl N-methyl-N-phenylcarbamothioate Structure

87463-11-4

O-methyl N-meth...

Chloro(chlorosulfanyl)oxomethane Structure

2757-23-5

Chloro(chlorosu...

N-Methylaniline Structure

100-61-8

N-Methylaniline

~%

S-(N-methylanilino) N-methyl-N-phenylcarbamothioate Structure

87463-10-3

S-(N-methylanil...

Detail
O-ethyl N-methyl-N-phenylthiocarbamate Structure

87463-00-1

O-ethyl N-methy...

Chloro(chlorosulfanyl)oxomethane Structure

2757-23-5

Chloro(chlorosu...

N-Methylaniline Structure

100-61-8

N-Methylaniline

~%

monochloroethane Structure

75-00-3

monochloroethane

Detail
O-isopropyl N-methyl-N-phenylthiocarbamate Structure

100244-42-6

O-isopropyl N-m...

~%

3-METHYL-2(3H)-BENZOTHIAZOLONE Structure

2786-62-1

3-METHYL-2(3H)-...

carbaniloyl chloride, n-methyl- Structure

4285-42-1

carbaniloyl chl...

O-methyl N-methyl-N-phenylcarbamothioate Structure

87463-11-4

O-methyl N-meth...

~%

3-METHYL-2(3H)-BENZOTHIAZOLONE Structure

2786-62-1

3-METHYL-2(3H)-...

carbaniloyl chloride, n-methyl- Structure

4285-42-1

carbaniloyl chl...

O-ethyl N-methyl-N-phenylthiocarbamate Structure

87463-00-1

O-ethyl N-methy...

~%

3-METHYL-2(3H)-BENZOTHIAZOLONE Structure

2786-62-1

3-METHYL-2(3H)-...

carbaniloyl chloride, n-methyl- Structure

4285-42-1

carbaniloyl chl...

Bis(N-methyl-N-phenylcarbamoyl)disulfane Structure

51480-12-7

Bis(N-methyl-N-...

~%

3-METHYL-2(3H)-BENZOTHIAZOLONE Structure

2786-62-1

3-METHYL-2(3H)-...

carbaniloyl chloride, n-methyl- Structure

4285-42-1

carbaniloyl chl...

O-isopropyl N-methyl-N-phenylthiocarbamate Structure

100244-42-6

O-isopropyl N-m...

~%

3-METHYL-2(3H)-BENZOTHIAZOLONE Structure

2786-62-1

3-METHYL-2(3H)-...

carbaniloyl chloride, n-methyl- Structure

4285-42-1

carbaniloyl chl...

(N-methyl-N-phenylcarbamoyl)sulfenyl chloride Structure

100244-53-9

(N-methyl-N-phe...

N-Methylaniline Structure

100-61-8

N-Methylaniline

~%

3-METHYL-2(3H)-BENZOTHIAZOLONE Structure

2786-62-1

3-METHYL-2(3H)-...

carbaniloyl chloride, n-methyl- Structure

4285-42-1

carbaniloyl chl...

O-isopropyl N-methyl-N-phenylthiocarbamate Structure

100244-42-6

O-isopropyl N-m...

N-Methylaniline Structure

100-61-8

N-Methylaniline

~%

3-METHYL-2(3H)-BENZOTHIAZOLONE Structure

2786-62-1

3-METHYL-2(3H)-...

carbaniloyl chloride, n-methyl- Structure

4285-42-1

carbaniloyl chl...

Detail
N-methyl-N-trimethylsilylaniline Structure

17890-34-5

N-methyl-N-trim...

~%

3-METHYL-2(3H)-BENZOTHIAZOLONE Structure

2786-62-1

3-METHYL-2(3H)-...

carbaniloyl chloride, n-methyl- Structure

4285-42-1

carbaniloyl chl...

N,4-Dimethylaniline Structure

623-08-5

N,4-Dimethylaniline

O-isopropyl N-methyl-N-phenylthiocarbamate Structure

100244-42-6

O-isopropyl N-m...

Chloro(chlorosulfanyl)oxomethane Structure

2757-23-5

Chloro(chlorosu...

~0%

Structure

1327166-56-2

Detail
S-(N-methylanilino) N-methyl-N-phenylcarbamothioate Structure

87463-10-3

S-(N-methylanil...

~98%

3-METHYL-2(3H)-BENZOTHIAZOLONE Structure

2786-62-1

3-METHYL-2(3H)-...

N-methylaniline,hydrochloride Structure

2739-12-0

N-methylaniline...

S-(N-methylanilino) N-methyl-N-phenylcarbamothioate Structure

87463-10-3

S-(N-methylanil...

~%

3-METHYL-2(3H)-BENZOTHIAZOLONE Structure

2786-62-1

3-METHYL-2(3H)-...

N-methylaniline,hydrochloride Structure

2739-12-0

N-methylaniline...

(N-methyl-N-phenylcarbamoyl)sulfenyl chloride Structure

100244-53-9

(N-methyl-N-phe...

N-Methylaniline Structure

100-61-8

N-Methylaniline

~%

N,4-Dimethylaniline, HCl Structure

2739-05-1

N,4-Dimethylani...

Benzenamine,N,2,6-trimethyl- Structure

767-71-5

Benzenamine,N,2...

O-isopropyl N-methyl-N-phenylthiocarbamate Structure

100244-42-6

O-isopropyl N-m...

Chloro(chlorosulfanyl)oxomethane Structure

2757-23-5

Chloro(chlorosu...

~%

N/A Structure

1327166-40-4

N/A

Detail

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