3-Aminobenzonitrile → HCID 22318884, compound

HRID 497312Notes

Reaction equation

HRID 497312 reaction equation
[Cl:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([N:11]=[C:12]=[O:13])=[CH:7][CH:6]=1)(=[O:4])=[O:3].[NH2:14][C:15]1[CH:16]=[C:17]([CH:20]=[CH:21][CH:22]=1)[C:18]#[N:19]>C(Cl)Cl.[N-]=C=O>[C:18]([C:17]1[CH:16]=[C:15]([NH:14][C:12](=[O:13])[NH:11][C:8]2[CH:7]=[CH:6][C:5]([S:2]([Cl:1])(=[O:4])=[O:3])=[CH:10][CH:9]=2)[CH:22]=[CH:21][CH:20]=1)#[N:19]

Participants

5

Reactant 2

HCID 167023-AminobenzonitrileHCID 81230p-Isocyanatobenzenesulphonyl chloride

Product 1

HCID 22318884HCID 22318884, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 105034IsocyanateSolvent

Procedure

A solution of 5.00 g (1 eq.) of 4-chlorosulfonylphenylisocyanate in anhydrous DCM (40 ml) was added to a solution of 3-aminobenzonitrile (2.71 g, 1 eq.) in anhydrous isocyanate (60 ml) at rt under inert atmosphere and the mixture was stirred overnight. The precipitate was filtered off to yield 7.3 g (95%) of 4-[3-(3-cyanophenyl)-ureido]-benzenesulfonyl chloride.

Workup

  1. filtrationThe precipitate was filtered off

Sources & evidence

ORD record
ord-db950d8e66864a5ea27fb63339ff71c4
Source dataset
uspto-grants-2005_09
Patent number
US06949567B2

Reaction notes

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