2-Aminothiazole → 1-(1-Methylbutoxy)-2-nitrobenzene

HRID 1983295Notes

Reaction equation

HRID 1983295 reaction equation
[CH3:1][CH:2]([OH:6])[CH2:3][CH2:4][CH3:5].F[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[N+:14]([O-:16])=[O:15].[CH3:17][CH:18]([O:22][C:23]1[CH:29]=[CH:28][CH:27]=[CH:26][C:24]=1[NH2:25])[CH2:19][CH2:20][CH3:21].[NH2:30][C:31]1[S:32][CH:33]=[CH:34][N:35]=1>>[CH3:1][CH:2]([O:6][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[N+:14]([O-:16])=[O:15])[CH2:3][CH2:4][CH3:5].[CH3:17][CH:18]([O:22][C:23]1[CH:29]=[CH:28][CH:27]=[CH:26][C:24]=1[NH:25][C:2]([NH:30][C:31]1[S:32][CH:33]=[CH:34][N:35]=1)=[O:6])[CH2:19][CH2:20][CH3:21]

Participants

6

Reactant 4

HCID 21552-AminothiazoleHCID 223862-PentanolHCID 738951-Fluoro-2-nitrobenzeneHCID 17605460HCID 17605460, compound2×

Product 2

HCID 59732798HCID 59732798, compoundYield 62%HCID 669987051-(1-Methylbutoxy)-2-nitrobenzeneYield 74%

Procedure

2-(2-Pentoxy)-1-nitrobenzene (387 mg, 74%) was prepared from 2-pentanol (0.27 ml, 2.5 mmol) and 1-fluoro-2-nitrobenzene (0.36 g, 2.5 mmol) following the general procedure G. This was reduced to 2-(2-pentoxy)aniline (0.26 g, 79%) following general procedure B. N-[2-(2-pentoxy)phenyl]-N′-(thiazol-2-yl)urea (280 mg, 62%) was prepared from 2-(2-pentoxy)aniline (0.25 g, 1.5 mmol) and 2-aminothiazole (150 mg, 1.5 mmol) following the general procedure D.

Sources & evidence

ORD record
ord-364dea298d9e43e18b546956c639ddd6
Source dataset
uspto-grants-2009_06
Patent number
US07541373B2

Reaction notes

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