Chlorosulfonic acid → 2-Carbamoylmethoxyphenoxyacetamide

HRID 411611Notes

Reaction equation

HRID 411611 reaction equation
[C:1]([CH2:4][O:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[O:12][CH2:13][C:14](=[O:16])[NH2:15])(=[O:3])[NH2:2].[Cl:17][S:18](O)(=[O:20])=[O:19]>C(Cl)(Cl)Cl>[C:14]([CH2:13][O:12][C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=1[O:5][CH2:4][C:1](=[O:3])[NH2:2])(=[O:16])[NH2:15].[C:14]([CH2:13][O:12][C:7]1[CH:8]=[C:9]([S:18]([Cl:17])(=[O:20])=[O:19])[CH:10]=[CH:11][C:6]=1[O:5][CH2:4][C:1](=[O:3])[NH2:2])(=[O:16])[NH2:15]

Participants

5

Reactant 2

HCID 24638Chlorosulfonic acidHCID 6995662-Carbamoylmethoxyphenoxyacetamide

Product 2

HCID 6995662-CarbamoylmethoxyphenoxyacetamideHCID 185412373,4-Bis(carbamoylmethoxy)benzenesulfonyl chloride

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
60 °C

Procedure

1,2-Bis(carbamoylmethoxy)benzene was prepared by a known method (H-S Kim. et al., (1998) J. Heterocyclic Chem., 35, 177-181). 1,2-Bis(carbamoylmethoxy)benzene (4.4 g) was added to chlorosulfonic acid (13 ml) at 0° C. with good stirring. Chloroform (4 ml) was added and warmed to about 60° C. for 2 hours. The reaction mixture was poured into chopped ice. The precipitates were collected, and washed with cold water. The solids were again washed with acetonitrile, and dried in vacuo to yield the title compound (4.9g).

Workup

  1. additionThe reaction mixture was poured into chopped ice
  2. customThe precipitates were collected
  3. washwashed with cold water
  4. washThe solids were again washed with acetonitrile
  5. customdried in vacuo

Sources & evidence

ORD record
ord-dc85092f010c491aa8b0bb98cf79d682
Source dataset
uspto-grants-2003_05
Patent number
US06559167B1

Reaction notes

Loading…