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

HRID 131856Notes

Reaction equation

HRID 131856 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][OH:5].F[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[N+:13]([O-:15])=[O:14].[CH3:16][O:17][CH2:18][CH2:19][O:20][C:21]1[CH:27]=[CH:26][CH:25]=[CH:24][C:22]=1[NH2:23].[NH2:28][C:29]1[S:30][CH:31]=[CH:32][N:33]=1>>[CH3:1][O:2][CH2:3][CH2:4][O:5][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[N+:13]([O-:15])=[O:14].[CH3:16][O:17][CH2:18][CH2:19][O:20][C:21]1[CH:27]=[CH:26][CH:25]=[CH:24][C:22]=1[NH:23][C:4]([NH:28][C:29]1[S:30][CH:31]=[CH:32][N:33]=1)=[O:5]

Participants

6

Reactant 4

HCID 21552-AminothiazoleHCID 80192-MethoxyethanolHCID 738951-Fluoro-2-nitrobenzeneHCID 30183712-(2-Methoxyethoxy)aniline2×

Product 2

HCID 30173611-(2-Methoxyethoxy)-2-nitrobenzeneYield 64%HCID 47392963HCID 47392963, compoundYield 55%

Procedure

2-(2-Methoxyethoxy)-1-nitrobenzene (0.25 g, 64%) was prepared from 2-methoxyethanol (0.16 ml, 2.0 mmol) and 1-fluoro-2-nitrobenzene (0.21 ml, 2.0 mmol) following the general procedure G. This was reduced to 2-(2-methoxyethoxy)aniline (0.13 g, 60%) following general procedure B. N-[2-(2-Methoxyethoxy)phenyl]-N′-(thiazol-2-yl)urea (115 mg, 55%) was prepared from 2-(2-methoxyethoxy)aniline (115 mg, 0.7 mmol) and 2-aminothiazole (140 mg, 1.4 mmol) following the general procedure D.

Sources & evidence

ORD record
ord-536b7e571b5047cd9c960192ee575c86
Source dataset
uspto-grants-2008_06
Patent number
US07384967B2

Reaction notes

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