2-Aminothiazole → 4-Nitro-3-(tetrahydro-furan-2-ylmethoxy)-toluene

HRID 599089

Reaction equation

HRID 599089 reaction equation
[O:1]1[CH2:5][CH2:4][CH2:3][CH:2]1[CH2:6][OH:7].F[C:9]1[CH:10]=[C:11]([CH3:18])[CH:12]=[CH:13][C:14]=1[N+:15]([O-:17])=[O:16].[CH3:19][C:20]1[CH:26]=[CH:25][C:23]([NH2:24])=[C:22]([O:27][CH2:28][CH:29]2[CH2:33][CH2:32][CH2:31][O:30]2)[CH:21]=1.[NH2:34][C:35]1[S:36][CH:37]=[CH:38][N:39]=1>>[N+:15]([C:14]1[CH:13]=[CH:12][C:11]([CH3:18])=[CH:10][C:9]=1[O:7][CH2:6][CH:2]1[CH2:3][CH2:4][CH2:5][O:1]1)([O-:17])=[O:16].[CH3:19][C:20]1[CH:26]=[CH:25][C:23]([NH:24][C:6]([NH:34][C:35]2[S:36][CH:37]=[CH:38][N:39]=2)=[O:7])=[C:22]([O:27][CH2:28][CH:29]2[CH2:33][CH2:32][CH2:31][O:30]2)[CH:21]=1

Participants

6

Reactant 4

HCID 21552-AminothiazoleHCID 7360Tetrahydrofurfuryl alcoholHCID 67966Benzene, 2-fluoro-4-methyl-1-nitro-HCID 246998844-Methyl-2-(oxolan-2-ylmethoxy)aniline2×

Product 2

HCID 597329951-[4-Methyl-2-(tetrahydro-furan-2-ylmethoxy)-phenyl]-3-thiazol-2-yl-ureaYield 71%HCID 669993474-Nitro-3-(tetrahydro-furan-2-ylmethoxy)-tolueneYield 75%

Procedure

4-Nitro-3-(tetrahydro-furan-2-ylmethoxy)-toluene (0.88 g, 75%) was prepared from tetrahydro-furan-2-ylmethanol and 3-fluoro-4-nitrotoluene (0.77 g, 5.0 mmol) following the general procedure G. This was reduced to 4-methyl-2-(tetrahydro-furan-2-ylmethoxy)-aniline (0.50 g, 65%) following general procedure C. 1-[4-Methyl-2-(tetrahydro-furan-2-ylmethoxy)-phenyl]-3-thiazol-2-yl-urea (236 mg, 71%) was prepared from 4-methyl-2-(tetrahydro-furan-2-ylmethoxy)-aniline (207 mg, 1.0 mmol) and 2-aminothiazole (100 mg, 1.0 mmol) following the general procedure D.

Sources & evidence

ORD record
ord-0d45099e3a594c8689a33459bf22f84c
Source dataset
uspto-grants-2011_03
Patent number
US07897628B2

Linked notes

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