2-Aminothiazole → 3-(3-Methyl-butoxy)-4-nitrotoluene

HRID 559997Notes

Reaction equation

HRID 559997 reaction equation
F[C:2]1[CH:3]=[C:4]([CH3:11])[CH:5]=[CH:6][C:7]=1[N+:8]([O-:10])=[O:9].[CH3:12][C:13]1[CH:19]=[CH:18][C:16]([NH2:17])=[C:15]([O:20][CH2:21][CH2:22][CH:23]([CH3:25])[CH3:24])[CH:14]=1.[NH2:26][C:27]1[S:28][CH:29]=[CH:30][N:31]=1.CC(C)C[CH2:35][OH:36]>>[CH3:12][CH:13]([CH3:19])[CH2:14][CH2:15][O:20][C:2]1[CH:3]=[C:4]([CH3:11])[CH:5]=[CH:6][C:7]=1[N+:8]([O-:10])=[O:9].[CH3:12][C:13]1[CH:19]=[CH:18][C:16]([NH:17][C:35]([NH:26][C:27]2[S:28][CH:29]=[CH:30][N:31]=2)=[O:36])=[C:15]([O:20][CH2:21][CH2:22][CH:23]([CH3:25])[CH3:24])[CH:14]=1

Participants

6

Reactant 4

HCID 21552-AminothiazoleHCID 31260Isoamyl AlcoholHCID 67966Benzene, 2-fluoro-4-methyl-1-nitro-HCID 261895264-Methyl-2-(3-methylbutoxy)aniline2×

Product 2

HCID 597326981-[4-Methyl-2-(3-methyl-butoxy)-phenyl]-3-thiazol-2-yl-ureaYield 76%HCID 669990283-(3-Methyl-butoxy)-4-nitrotolueneYield 80%

Procedure

3-(3-Methyl-butoxy)-4-nitrotoluene (0.89 g, 80%) was prepared from 3-methylbutanol and 3-fluoro-4-nitrotoluene (0.77 g, 5.0 mmol) following the general procedure G. This was reduced to 4-methyl-2-(3-methylbutoxy)aniline (0.55 g, 72%) following general procedure C. 1-[4-Methyl-2-(3-methyl-butoxy)-phenyl]-3-thiazol-2-yl-urea (240 mg, 76%) was prepared from 4-methyl-2-(3-methyl-butoxy)aniline (193 mg, 1.0 mmol) and 2-aminothiazole (100 mg, 1.0 mmol) following the general procedure D.

Sources & evidence

ORD record
ord-0b08c2c3bcc24d29b715cc2212dc7ec8
Source dataset
uspto-grants-2011_11
Patent number
US08063081B2

Reaction notes

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