Dichloromethane → 3,4-Bis(carbamoylmethoxy)benzenesulfonyl chloride

HRID 1593251Notes

Reaction equation

HRID 1593251 reaction equation
[C:1]([CH2:4][O:5][C:6]1[CH:16]=[CH:15][CH:14]=[CH:13][C:7]=1[O:8][CH2:9][C:10]([NH2:12])=[O:11])(=[O:3])[NH2:2].[Cl:17][S:18](O)(=[O:20])=[O:19].ClCCl>O>[C:10]([CH2:9][O:8][C:7]1[CH:13]=[C:14]([S:18]([Cl:17])(=[O:20])=[O:19])[CH:15]=[CH:16][C:6]=1[O:5][CH2:4][C:1]([NH2:2])=[O:3])(=[O:11])[NH2:12]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 24638Chlorosulfonic acidHCID 6995662-Carbamoylmethoxyphenoxyacetamide

Product 1

HCID 185412373,4-Bis(carbamoylmethoxy)benzenesulfonyl chlorideYield 77.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

2-Carbamoylmethoxyphenoxyacetamide (Intermediate A64, 112 g, 0.50 mol) was added portion wise over 15 min to rapidly stirred chlorosulfonic acid (582.5 g, 5.0 mol) and cooled to 0° C. Then dichloromethane (120 mL) was added, and the mixture was heated in a 60°-70° C. bath for 3 hr. The mixture was slowly poured into 1.5 Kg of crushed ice, and water (500 mL) was added. The resulting solid was collected, washed with water and acetone, resuspended in acetone, filtered, washed with acetone, and air dried to yield 125 g (77%) of the title compound.

Workup

  1. temperaturethe mixture was heated in a 60°-70° C. bath for 3 hr
  2. additionwas added
  3. customThe resulting solid was collected
  4. washwashed with water and acetone
  5. filtrationfiltered
  6. washwashed with acetone, and air
  7. customdried

Sources & evidence

ORD record
ord-cb234e207ced4b2d9037aeb1c0430385
Source dataset
uspto-grants-2007_11
Patent number
US07294716B2

Reaction notes

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