1-Bromo-2-isothiocyanatobenzene → N-[4-Chloro-2-hydroxy-3-[N'',N''-dimethylaminosulfonyl]phenyl]-N'-(2-bromophenyl)thiourea

HRID 1840352Notes

Reaction equation

HRID 1840352 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].[Br:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[N:23]=[C:24]=[S:25]>C(O)C>[Cl:12][C:11]1[CH:10]=[CH:9][C:8]([NH:13][C:24]([NH:23][C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=2[Br:16])=[S:25])=[C:7]([OH:14])[C:6]=1[S:3]([N:2]([CH3:15])[CH3:1])(=[O:5])=[O:4]

Participants

4

Reactant 2

HCID 6116541-Bromo-2-isothiocyanatobenzeneHCID 23447758N,N-Dimethyl-3-amino-6-chloro-2-hydroxybenzenesulfonamide

Product 1

HCID 10183328N-[4-Chloro-2-hydroxy-3-[N'',N''-dimethylaminosulfonyl]phenyl]-N'-(2-bromophenyl)thioureaYield 22.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of N,N-dimethyl-3-amino-6-chloro-2-hydroxybenzene sulfonamide (480 mg, 3.58 mmol) and 2-bromophenylisothiocyanate (0.53 μL, 3.94 mmol) in 10 mL of ethanol was stirred at room temperature for overnight. Purification by column chromatography on silica gel, eluting with ethyl acetate/hexane (gradient elution) gave the desired product (368 mg, 22%). EI-MS (m/z) 463.67, 465.66, 467.65, 468.64 (M+).

Workup

  1. customPurification by column chromatography on silica gel
  2. washeluting with ethyl acetate/hexane (gradient elution)

Sources & evidence

ORD record
ord-a20d9a8e97254a5c972e6e49909868eb
Source dataset
uspto-grants-2004_01
Patent number
US06680317B2

Reaction notes

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