Butyl isocyanate → 3-Chloro-4-isocyanatobenzenesulfonyl isocyanate

HRID 1452055Notes

Reaction equation

HRID 1452055 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH2:11])(=[O:10])=[O:9])=[CH:4][C:3]=1[Cl:12].C(N=[C:18]=[O:19])CCC.C(Cl)(=O)[C:21](Cl)=[O:22]>ClC1C=CC=CC=1>[Cl:12][C:3]1[CH:4]=[C:5]([S:8]([N:11]=[C:18]=[O:19])(=[O:9])=[O:10])[CH:6]=[CH:7][C:2]=1[N:1]=[C:21]=[O:22]

Participants

5

Reactant 3

HCID 8110Butyl isocyanateHCID 65578Oxalyl chlorideHCID 15020144-Amino-3-chlorobenzenesulfonamide

Product 1

HCID 221828253-Chloro-4-isocyanatobenzenesulfonyl isocyanate

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Conditions

Temperature
100 °C

Procedure

5,7-Dichloro-4-[4-(methylcarbamoyl)-3-chlorobenzenesulfonimide]-1,4-dihydroquinoline-2-carboxylic acid, methyl ester ##STR38## Dissolve 4-amino-3-chlorobenzenesulfonamide (0.96g, 5mmol) in chlorobenzene (10% solution) and distill the mixture to remove any traces of water. Cool to 100° C. and add n-butyl isocyanate (99mg, 1mmol). Heat to reflux and add, by dropwise addition, oxalyl chloride (1.5mL). Purge with nitrogen at 130°-132° C. for 30 minutes and distill to give 3-chloro-4-isocyanatobenzenesulfonyl isocyanate.

Workup

  1. distillationdistill the mixture
  2. customto remove any traces of water
  3. temperatureHeat
  4. temperatureto reflux
  5. customPurge with nitrogen at 130°-132° C. for 30 minutes
  6. distillationdistill

Sources & evidence

ORD record
ord-32d90dac3ffb46b38936df6f2c697a48
Source dataset
uspto-grants-1997_02
Patent number
US05606063

Reaction notes

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