Ethyl N-phenylcarbamate → (4-Chlorosulfonyl-phenyl)-carbamic acid ethyl ester

HRID 2182433

Reaction equation

HRID 2182433 reaction equation
[C:1]1([NH:7][C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cl:13][S:14](O)(=[O:16])=[O:15]>>[CH2:11]([O:10][C:8](=[O:9])[NH:7][C:1]1[CH:6]=[CH:5][C:4]([S:14]([Cl:13])(=[O:16])=[O:15])=[CH:3][CH:2]=1)[CH3:12]

Participants

3

Reactant 2

HCID 7591Ethyl N-phenylcarbamateHCID 24638Chlorosulfonic acid

Product 1

HCID 256294(4-Chlorosulfonyl-phenyl)-carbamic acid ethyl ester

Conditions

Temperature
60 °C

Procedure

To a stirred solution of chlorosulfonic acid (20 ml) at 0° C., was added N-phenylurethane (9.90 g) at such a rate that the temperature did not exceed 20° C. The reaction was then heated at 60° C. for 3 hours, cooled to ambient temperature and poured carefully onto ice. The resultant precipitate was collected by filtration and dried in vacuo to give (4-chlorosulfonyl-phenyl)-carbamic acid ethyl ester (14.50 g) as an off-white solid. LC-MS (METHOD B): RT=3.11 minutes, 284.23 (M+H)+.

Workup

  1. customdid not exceed 20° C
  2. temperaturecooled to ambient temperature
  3. additionpoured carefully onto ice
  4. filtrationThe resultant precipitate was collected by filtration
  5. customdried in vacuo

Sources & evidence

ORD record
ord-193f8b39b2fb4ac7b90f7b62d37db764
Source dataset
uspto-grants-2005_05
Patent number
US06897208B2

Linked notes

Loading…