2,3-Dichlorophenyl Isothiocyanate → N-[4-Chloro-2-hydroxy-3[N'',N''-dimethylaminosulfonyl]phenyl]-N'-(2,3-dichlorophenyl)thiourea

HRID 1840335Notes

Reaction equation

HRID 1840335 reaction equation
[CH3:1][N:2]([CH3:15])[S:3]([C:6]1[C:11]([Cl:12])=[CH:10][CH:9]=[C:8]([NH2:13])[C:7]=1[OH:14])(=[O:5])=[O:4].[Cl:16][C:17]1[C:22]([Cl:23])=[CH:21][CH:20]=[CH:19][C:18]=1[N:24]=[C:25]=[S:26]>CN(C)C=O>[Cl:12][C:11]1[CH:10]=[CH:9][C:8]([NH:13][C:25]([NH:24][C:18]2[CH:19]=[CH:20][CH:21]=[C:22]([Cl:23])[C:17]=2[Cl:16])=[S:26])=[C:7]([OH:14])[C:6]=1[S:3]([N:2]([CH3:15])[CH3:1])(=[O:5])=[O:4]

Participants

4

Reactant 2

HCID 27962812,3-Dichlorophenyl IsothiocyanateHCID 23447758N,N-Dimethyl-3-amino-6-chloro-2-hydroxybenzenesulfonamide

Product 1

HCID 10297913N-[4-Chloro-2-hydroxy-3[N'',N''-dimethylaminosulfonyl]phenyl]-N'-(2,3-dichlorophenyl)thioureaYield 68.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of N,N-dimethyl-3-amino-6-chloro-2-hydroxybenzenesulfonamide (356 mg, 1.42 mmol) and 2,3-dichlorophenylisothiocyanate (318 mg, 1.57 mmol) in 1.0 mL of N,N-dimethylformamide was stirred at room temperature for 3 hours. Purification by column chromatography on silica gel, eluting with ethyl acetate/hexane (30/70, v/v) to give the desired product (440 mg, 68%). EI-MS (m/z) 455.5 (M+).

Workup

  1. customPurification by column chromatography on silica gel
  2. washeluting with ethyl acetate/hexane (30/70

Sources & evidence

ORD record
ord-9c77694859774a4391209ab3369f9749
Source dataset
uspto-grants-2004_01
Patent number
US06680317B2

Reaction notes

Loading…