Ethanesulfonyl chloride → Ethanesulfonamide, N-[2,6-dimethyl-4-[[(methylamino)carbonyl]oxy]phenyl]-

HRID 2072437Notes

Reaction equation

HRID 2072437 reaction equation
[CH3:1][NH:2][C:3](=[O:14])[O:4][C:5]1[CH:10]=[C:9]([CH3:11])[C:8]([NH2:12])=[C:7]([CH3:13])[CH:6]=1.[CH2:15]([S:17](Cl)(=[O:19])=[O:18])[CH3:16]>N1C=CC=CC=1>[CH3:1][NH:2][C:3](=[O:14])[O:4][C:5]1[CH:10]=[C:9]([CH3:11])[C:8]([NH:12][S:17]([CH2:15][CH3:16])(=[O:19])=[O:18])=[C:7]([CH3:13])[CH:6]=1

Participants

4

Reactant 2

HCID 11667Ethanesulfonyl chlorideHCID 13252Aminozectran

Product 1

HCID 163064Ethanesulfonamide, N-[2,6-dimethyl-4-[[(methylamino)carbonyl]oxy]phenyl]-

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
42 °C

Procedure

3,5-Dimethyl-4-aminophenyl N-methylcarbamate (1.0g., 0.0052 mole), prepared according to the general directions of A. T. Shulgin, U.S. Pat. No. 3,084,098 was dissolved in 5 ml. of pyridine. To this solution was added ethanesulfonyl chloride (0.68g., and 0.0053 mole) and after being stirred for about 20 minutes the reaction solution was warmed briefly at 42° C. Quenching the reaction solution in excess water yielded brown solids which upon being recrystallized from ethanol/water melted at 171°-73° C. (0.85g.).

Workup

  1. dissolution3,084,098 was dissolved in 5 ml
  2. customQuenching the reaction solution in excess water yielded brown solids which
  3. customupon being recrystallized from ethanol/water melted at 171°-73° C. (0.85g.)

Sources & evidence

ORD record
ord-f408ba6b8ee543b2ae846a37b0482f75
Source dataset
uspto-grants-1977_09
Patent number
US04051254

Reaction notes

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