Oxalyl chloride → HCID 85982025, compound

HRID 2250566Notes

Reaction equation

HRID 2250566 reaction equation
[CH2:1]([O:8][C:9]([NH:11][S:12]([C:15]1[CH:23]=[CH:22][C:18]([C:19](O)=[O:20])=[CH:17][CH:16]=1)(=[O:14])=[O:13])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(Cl)(=O)C([Cl:27])=O>ClCCl.CN(C)C=O>[Cl:27][C:19]([C:18]1[CH:22]=[CH:23][C:15]([S:12]([NH:11][C:9](=[O:10])[O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)(=[O:14])=[O:13])=[CH:16][CH:17]=1)=[O:20]

Participants

5

Reactant 2

HCID 65578Oxalyl chloride2×HCID 574445324-({[(Benzyloxy)carbonyl]amino}sulfonyl)benzoic acid

Product 1

HCID 85982025HCID 85982025, compoundYield 78.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a suspension of 4-({[(benzyloxy)carbonyl]amino}-sulfonyl)benzoic acid (2.90 g) in dichloromethane (30 mL) was added N,N-dimethylformamide (19.0 mg) and followed by oxalyl chloride (1.15 g) under an ice-bath. The mixture was stirred for 0.5 hour at room temperature and refluxed for 1 hour. The resulting mixture was refluxed further for 5 minutes after adding oxalyl chloride (439 mg). The volatile was evaporated off to give a white solid. The solid was triturated in diisopropyl ether to give benzyl [4-(chlorocarbonyl)phenyl]sulfonylcarbamate as a white powder (2.40 g), which was used for the next reaction without further purification.

Workup

  1. temperaturerefluxed for 1 hour
  2. temperatureThe resulting mixture was refluxed further for 5 minutes
  3. customThe volatile was evaporated off
  4. customto give a white solid
  5. customThe solid was triturated in diisopropyl ether

Sources & evidence

ORD record
ord-f28fa450d7ac4de697cf92883c02854b
Source dataset
uspto-grants-2008_01
Patent number
US07317009B2

Reaction notes

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