2-Aminothiazole → 2-(Cyclopropylmethoxy)-4-methyl-1-nitrobenzene

HRID 1983393Notes

Reaction equation

HRID 1983393 reaction equation
[CH:1]1([CH2:4][OH:5])[CH2:3][CH2:2]1.F[C:7]1[CH:8]=[C:9]([CH3:16])[CH:10]=[CH:11][C:12]=1[N+:13]([O-:15])=[O:14].[CH:17]1([CH2:20][O:21][C:22]2[CH:28]=[C:27]([CH3:29])[CH:26]=[CH:25][C:23]=2[NH2:24])[CH2:19][CH2:18]1.[NH2:30][C:31]1[S:32][CH:33]=[CH:34][N:35]=1>>[CH:1]1([CH2:4][O:5][C:7]2[CH:8]=[C:9]([CH3:16])[CH:10]=[CH:11][C:12]=2[N+:13]([O-:15])=[O:14])[CH2:3][CH2:2]1.[CH:17]1([CH2:20][O:21][C:22]2[CH:28]=[C:27]([CH3:29])[CH:26]=[CH:25][C:23]=2[NH:24][C:4]([NH:30][C:31]2[S:32][CH:33]=[CH:34][N:35]=2)=[O:5])[CH2:18][CH2:19]1

Participants

6

Reactant 4

HCID 21552-AminothiazoleHCID 67966Benzene, 2-fluoro-4-methyl-1-nitro-HCID 75644CyclopropanemethanolHCID 435600402-(Cyclopropylmethoxy)-4-methylaniline2×

Product 2

HCID 59732787HCID 59732787, compoundYield 72%HCID 669988732-(Cyclopropylmethoxy)-4-methyl-1-nitrobenzeneYield 75%

Procedure

3-Cyclopropylmethoxy-4-nitrotoluene (0.77 g, 75%) was prepared from cyclopropylmethanol and 3-fluoro-4-nitrotoluene (0.77 g, 5.0 mmol) following the general procedure G. This was reduced to 2-cyclopropylmethoxy-4-methyl-aniline (0.47 g, 71%) following general procedure C. 1-(2-Cyclopropylmethoxy-4-methyl-phenyl)-3-thiazol-2-yl-urea (218 mg, 72%) was prepared from 2-cyclopropylmethoxy-4-methyl-aniline (177 mg, 1.0 mmol) and 2-aminothiazole (100 mg, 1.0 mmol) following the general procedure D.

Sources & evidence

ORD record
ord-ded330924c8c42a28a53d8c1466dfa2d
Source dataset
uspto-grants-2009_06
Patent number
US07541373B2

Reaction notes

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