2-Aminothiazole → 2-(3,5-Dimethylphenylsulfanyl)nitrobenzene

HRID 1983286Notes

Reaction equation

HRID 1983286 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([SH:9])[CH:5]=[C:6]([CH3:8])[CH:7]=1.F[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[N+:17]([O-:19])=[O:18].CC1C=[C:23]([S:28][C:29]2C=CC=C[C:30]=2[NH2:31])C=C(C)C=1.[NH2:36][C:37]1SC=C[N:41]=1>>[CH3:1][C:2]1[CH:3]=[C:4]([S:9][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[N+:17]([O-:19])=[O:18])[CH:5]=[C:6]([CH3:8])[CH:7]=1.[S:28]1[CH:29]=[CH:30][N:31]=[C:23]1[NH:36][C:37](=[O:18])[NH2:41]

Participants

6

Reactant 4

HCID 21552-AminothiazoleHCID 738951-Fluoro-2-nitrobenzeneHCID 1175483,5-DimethylbenzenethiolHCID 669989672-((3,5-Dimethylphenyl)thio)aniline2×

Product 2

HCID 167817081-(Thiazol-2-yl)ureaYield 74%HCID 669990172-(3,5-Dimethylphenylsulfanyl)nitrobenzeneYield 78%

Procedure

2-(3,5-Dimethylphenylsulfanyl)nitrobenzene (1.01 g, 78%) was prepared from 3,5-dimethylthiophenol (0.76 g, 5.5 mmol) and 2-fluoronitrobenzene (0.71 g, 5.0 mmol) following the general procedure A. This compound was reduced to 2-(3,5-dimethylphenylsulfanyl)-aniline (0.64 g, 72%) following the general procedure B. N-[2-3,5-Dimethylphenylsulfanyl)-phenyl]-N′-(thiazol-2-yl)urea (131 mg; 74%) was prepared from 2-(3,5-dimethylphenyl-sulfanyl)aniline (115 mg, 0.5 mmol) and 2-aminothiazole (60 mg, 0.6 mmol) following the general procedure D.

Sources & evidence

ORD record
ord-6ab0f95507a24a36a404e275372fe87e
Source dataset
uspto-grants-2009_06
Patent number
US07541373B2

Reaction notes

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