2-Aminothiazole → 1-(2-Isopropoxy-4-methyl-phenyl)-3-thiazol-2-yl-urea

HRID 1983391Notes

Reaction equation

FC1C=C(C)C=CC=1[N+]([O-])=O.[CH:12]([O:15][C:16]1[CH:22]=[C:21]([CH3:23])[CH:20]=[CH:19][C:17]=1[NH2:18])([CH3:14])[CH3:13].[NH2:24][C:25]1[S:26][CH:27]=[CH:28][N:29]=1.C[CH:31]([OH:33])C>>[CH:12]([O:15][C:16]1[CH:22]=[C:21]([CH3:23])[CH:20]=[CH:19][C:17]=1[NH:18][C:31]([NH:24][C:25]1[S:26][CH:27]=[CH:28][N:29]=1)=[O:33])([CH3:14])[CH3:13]

Participants

Reactant 4

HCID 21552-Aminothiazole

HCID 3776Isopropanol

HCID 67966Benzene, 2-fluoro-4-methyl-1-nitro-

HCID 150681144-Methyl-2-(propan-2-yloxy)aniline2×

Product 1

HCID 597329281-(2-Isopropoxy-4-methyl-phenyl)-3-thiazol-2-yl-ureaYield 62%

Procedure

3-(2-Isopropoxy)-4-nitrotoluene (0.72 g, 74%) was prepared from 2-propanol and 3-fluoro-4-nitrotoluene (0.77 g, 5.0 mmol) following the general procedure G. This was reduced to 2-isopropoxy-4-methyl-aniline (0.42 g, 70%) following general procedure C. 1-(2-Isopropoxy-4-methyl-phenyl)-3-thiazol-2-yl-urea (180 mg, 62%) was prepared from 2-isopropoxy-4-methyl-aniline (165 mg, 1.0 mmol) and 2-aminothiazole (100 mg, 1.0 mmol) following the general procedure D.

Sources & evidence

ORD record: ord-2fbe04104ce949a38aa505ad87c252bc
Source dataset: uspto-grants-2009_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07541373B2

Reaction notes

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