Thiourea → N-[4-Chloro-2-hydroxy-3-(N'',N''-dimethylaminosulfonyl)phenyl]-N'(2-chloro-4-fluorophenyl) thiourea

HRID 1840386Notes

Reaction equation

HRID 1840386 reaction equation
NC(N)=S.[CH3:5][N:6]([CH3:19])[S:7]([C:10]1[C:15]([Cl:16])=[CH:14][CH:13]=[C:12]([NH2:17])[C:11]=1[OH:18])(=[O:9])=[O:8].[Cl:20][C:21]1[CH:26]=[C:25]([F:27])[CH:24]=[CH:23][C:22]=1[N:28]=[C:29]=[S:30]>>[Cl:16][C:15]1[CH:14]=[CH:13][C:12]([NH:17][C:29]([NH:28][C:22]2[CH:23]=[CH:24][C:25]([F:27])=[CH:26][C:21]=2[Cl:20])=[S:30])=[C:11]([OH:18])[C:10]=1[S:7]([N:6]([CH3:19])[CH3:5])(=[O:9])=[O:8]

Participants

4

Reactant 3

HCID 2723790ThioureaHCID 27575812-Chloro-4-fluoro-1-isothiocyanatobenzeneHCID 23447758N,N-Dimethyl-3-amino-6-chloro-2-hydroxybenzenesulfonamide

Product 1

HCID 23447835N-[4-Chloro-2-hydroxy-3-(N'',N''-dimethylaminosulfonyl)phenyl]-N'(2-chloro-4-fluorophenyl) thioureaYield 55%

Procedure

Following the general procedure for thiourea formation outlined in example 12, N,N-dimethyl-3-amino-6-chloro-2-hydroxybenzenesulfonamide (526 mg, 2.10 mmol) and 2-chloro-4-fluorophenylisothiocyanate (586 mg, 3.1 mmol) were coupled to form the desired thiourea (505 mg, 55%). EI-MS m/z 437.75 (M−).

Sources & evidence

ORD record
ord-2c8095dfa51b447fa3cf4449934fcafe
Source dataset
uspto-grants-2004_01
Patent number
US06680317B2

Reaction notes

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