Guaiacol → HCID 66999029, compound

HRID 598950

Reaction equation

HRID 598950 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[OH:9].F[C:11]1[CH:16]=[CH:15][C:14]([S:17]([CH3:20])(=[O:19])=[O:18])=[CH:13][C:12]=1[N+:21]([O-:23])=[O:22].[CH3:24][O:25][C:26]1[CH:43]=[CH:42][CH:41]=[CH:40][C:27]=1[O:28][C:29]1[CH:35]=[CH:34][C:33]([S:36]([CH3:39])(=[O:38])=[O:37])=[CH:32][C:30]=1[NH2:31].[NH2:44][C:45]1[S:46][CH:47]=[CH:48][N:49]=1>>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[O:9][C:11]1[CH:16]=[CH:15][C:14]([S:17]([CH3:20])(=[O:19])=[O:18])=[CH:13][C:12]=1[N+:21]([O-:23])=[O:22].[CH3:24][O:25][C:26]1[CH:43]=[CH:42][CH:41]=[CH:40][C:27]=1[O:28][C:29]1[CH:35]=[CH:34][C:33]([S:36]([CH3:39])(=[O:37])=[O:38])=[CH:32][C:30]=1[NH:31][C:4]([NH:44][C:45]1[S:46][CH:47]=[CH:48][N:49]=1)=[O:9]

Participants

6

Reactant 4

HCID 460GuaiacolHCID 21552-AminothiazoleHCID 3131371-Fluoro-4-methanesulfonyl-2-nitrobenzeneHCID 43448157HCID 43448157, compound2×

Product 2

HCID 59732998N-[2-(2-Methoxyphenoxy)-5-(methylsulfonyl)phenyl]-N'-(thiazol-2-yl)ureaYield 65%HCID 66999029HCID 66999029, compoundYield 75%

Procedure

2-(2-Methoxyphenoxy)-5-(methylsulfonyl)-1-nitrobenzene (1.21 g, 75%) was prepared from 2-methoxyphenol (0.68 g, 5.5 mmol) and 1-fluoro-4-methylsulfonyl-2-nitro-benzene (1.09 g, 5.0 mmol) following the general procedure A. This was reduced to 2-(2-methoxyphenoxy)-5-(methylsulfonyl)aniline (0.68 g, 62%) following general procedure B. N-[2-(2-Methoxyphenoxy)-5-(methylsulfonyl)phenyl]-N′-(thiazol-2-yl)urea (136 mg, 65%) was prepared from 2-(2-methoxyphenoxy)-5-(methylsulfonyl)aniline (146 mg, 0.5 mmol) and 2-aminothiazole (60 mg, 0.6 mmol) following the general procedure D.

Sources & evidence

ORD record
ord-f8043a86384d4be9a3d4cad2616161f2
Source dataset
uspto-grants-2011_03
Patent number
US07897628B2

Linked notes

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