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

HRID 131846

Reaktionsgleichung

Reaktionsgleichung von HRID 131846
[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].[CH3:20][C:21]1[CH:22]=[C:23]([S:28][C:29]2[CH:35]=[CH:34][CH:33]=[CH:32][C:30]=2[NH2:31])[CH:24]=[C:25]([CH3:27])[CH:26]=1.[NH2:36][C:37]1SC=[CH:40][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.[CH3:27][C:25]1[CH:24]=[C:23]([S:28][C:29]2[CH:35]=[CH:34][CH:33]=[CH:32][C:30]=2[NH:31][C:40]([NH:41][C:37]2[S:9][CH:4]=[CH:3][N:36]=2)=[O:18])[CH:22]=[C:21]([CH3:20])[CH:26]=1

Komponenten

6

Edukt 4

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

Produkt 2

HCID 59733126N-[2-(3,5-Dimethylphenylsulfanyl)phenyl]-N'-(thiazol-2-yl)ureaAusbeute 74 %HCID 669990172-(3,5-Dimethylphenylsulfanyl)nitrobenzeneAusbeute 78 %

Versuchsvorschrift

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-dimethylphenylsulfanyl)aniline (115 mg, 0.5 mmol) and 2-aminothiazole (60 mg, 0.6 mmol) following the general procedure D.

Quellen und Nachweise

ORD-Eintrag
ord-e41ede9e832c434b94b3d4104ebcbf1e
Quelldatensatz
uspto-grants-2008_06
Patentnummer
US07384967B2

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