Oxalyl chloride → 3-Chlorobenzene-1-sulfonyl isocyanate

HRID 1452054Notes

Reaction equation

HRID 1452054 reaction equation
C(Cl)(=O)[C:2](Cl)=[O:3].[Cl:7][C:8]1[CH:9]=[C:10]([S:14]([NH2:17])(=[O:16])=[O:15])[CH:11]=[CH:12][CH:13]=1>ClC1C=CC=CC=1Cl>[Cl:7][C:8]1[CH:9]=[C:10]([S:14]([N:17]=[C:2]=[O:3])(=[O:15])=[O:16])[CH:11]=[CH:12][CH:13]=1

Participants

4

Reactant 2

HCID 65578Oxalyl chloride2×HCID 5193773-Chlorobenzenesulfonamide

Product 1

HCID 199734703-Chlorobenzene-1-sulfonyl isocyanateYield 40%

Reagents, catalysts & solvents 1

HCID 72391,2-DichlorobenzeneSolvent

Procedure

5,7-Dichloro-4-[3-chlorobenzenesulfonimide]-1,4-dihydroquinoline-2-carboxylic acid, methyl ester ##STR30## Combine oxalyl chloride (25mL) and 3-chlorobenzenesulfonamide (4.3g, 23mmol) and reflux overnight. Remove oxalyl chloride in vacuo and combine the resulting residue with o-dichlorobenzene (25mL) and reflux. Evaporate the solvent in vacuo to distill to give [3-chlorobenzenesulfonyl]isocyanate (2g, 40%); bp 92°-5° C.

Workup

  1. temperaturereflux
  2. customEvaporate the solvent in vacuo
  3. distillationto distill

Sources & evidence

ORD record
ord-8e13e076709544fbbd917889406f0e01
Source dataset
uspto-grants-1997_02
Patent number
US05606063

Reaction notes

Loading…