2-Aminothiazole → 3-(3-Methyl-but-2-enyloxy)-4-nitrotoluene

HRID 131950

Reaction equation

HRID 131950 reaction equation
[CH3:1][C:2]([CH3:6])=[CH:3][CH2:4][OH:5].F[C:8]1[CH:9]=[C:10]([CH3:17])[CH:11]=[CH:12][C:13]=1[N+:14]([O-:16])=[O:15].[CH3:18][C:19]1[CH:25]=[CH:24][C:22]([NH2:23])=[C:21]([O:26][CH2:27][CH:28]=[C:29]([CH3:31])[CH3:30])[CH:20]=1.[NH2:32][C:33]1[S:34][CH:35]=[CH:36][N:37]=1>>[CH3:1][C:2]([CH3:6])=[CH:3][CH2:4][O:5][C:8]1[CH:9]=[C:10]([CH3:17])[CH:11]=[CH:12][C:13]=1[N+:14]([O-:16])=[O:15].[CH3:18][C:19]1[CH:25]=[CH:24][C:22]([NH:23][C:4]([NH:32][C:33]2[S:34][CH:35]=[CH:36][N:37]=2)=[O:5])=[C:21]([O:26][CH2:27][CH:28]=[C:29]([CH3:31])[CH3:30])[CH:20]=1

Participants

6

Reactant 4

HCID 21552-AminothiazoleHCID 111733-Methyl-2-buten-1-OLHCID 67966Benzene, 2-fluoro-4-methyl-1-nitro-HCID 669984734-Methyl-2-(3-methyl-but-2-enyloxy)aniline2×

Product 2

HCID 597331341-[4-Methyl-2-(3-methyl-but-2-enyloxy)-phenyl]-3-thiazol-2-yl-ureaYield 65%HCID 669990963-(3-Methyl-but-2-enyloxy)-4-nitrotolueneYield 72%

Procedure

3-(3-methyl-but-2-enyloxy)-4-nitrotoluene (0.8 g, 72%) was prepared from 3-methylbut-2-en-1-ol and 3-fluoro-4-nitrotoluene (0.77 g, 5.0 mmol) following the general procedure G. This was reduced to 4-methyl-2-(3-methyl-but-2-enyloxy)aniline (0.43 g, 62%) following general procedure B. 1-[4-Methyl-2-(3-methyl-but-2-enyloxy)-phenyl]-3-thiazol-2-yl-urea (206 mg, 65%) was prepared from 4-methyl-2-(3-methyl-but-2-enyloxy)aniline (191 mg, 1.0 mmol) and 2-aminothiazole (100 mg, 1.0 mmol) following the general procedure D.

Sources & evidence

ORD record
ord-4ce1372183fc4b61a577b50e83009336
Source dataset
uspto-grants-2008_06
Patent number
US07384967B2

Linked notes

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