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

HRID 1593259Notes

Reaction equation

HRID 1593259 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]=[CH:14][C:15]([S:18]([Cl:17])(=[O:20])=[O:19])=[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 A84, 112 g, 0.50 mol) was added portion-wise over 15 min to rapidly stirred chlorosulfonic acid (582.5 g, 5.0 mol) cooled to 0° C. Dichloromethane (120 mL) was then 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 then water (500 mL) was added. The resulting solid was collected, washed with water (3×500 mL) and acetone (3×500 mL), resuspended in acetone (1 L), again collected, washed with acetone (500 mL), 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. customThe resulting solid was collected
  3. washwashed with water (3×500 mL) and acetone (3×500 mL)
  4. customagain collected
  5. washwashed with acetone (500 mL), and air
  6. customdried

Sources & evidence

ORD record
ord-c489dd80134348e7bb6a5427dbdd02ac
Source dataset
uspto-grants-2007_11
Patent number
US07294716B2

Reaction notes

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