Guaiacol → HCID 27815639, compound

HRID 2276118Notes

Reaction equation

HRID 2276118 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:18]=[CH:17][C:14]([C:15]#[N:16])=[CH:13][C:12]=1[N+:19]([O-:21])=[O:20].[CH3:22][O:23][C:24]1[CH:39]=[CH:38][CH:37]=[CH:36][C:25]=1[O:26][C:27]1[CH:34]=[CH:33][C:30]([C:31]#[N:32])=[CH:29][C:28]=1[NH2:35].[NH2:40][C:41]1[S:42][CH:43]=[CH:44][N:45]=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:18]=[CH:17][C:14]([C:15]#[N:16])=[CH:13][C:12]=1[N+:19]([O-:21])=[O:20].[C:31]([C:30]1[CH:33]=[CH:34][C:27]([O:26][C:25]2[CH:36]=[CH:37][CH:38]=[CH:39][C:24]=2[O:23][CH3:22])=[C:28]([NH:35][C:4]([NH:40][C:41]2[S:42][CH:43]=[CH:44][N:45]=2)=[O:9])[CH:29]=1)#[N:32]

Participants

6

Reactant 4

HCID 460GuaiacolHCID 21552-AminothiazoleHCID 27746544-Fluoro-3-nitrobenzonitrileHCID 43518248HCID 43518248, compound2×

Product 2

HCID 27815639HCID 27815639, compoundYield 81%HCID 59732835N-[5-Cyano-2-(2-methoxyphenoxy)phenyl]-N'-(thiazol-2-yl)ureaYield 71%

Procedure

4-(2-Methoxyphenoxy)-3-nitrobenzonitrile (1.10 g, 81%) was prepared from 2-methoxyphenol (0.68 g, 5.5 mmol) and 4-fluoro-3-nitrobenzonitrile (1.33 g, 5.0 mmol) following general procedure A. This was reduced to 4-(2-methoxyphenoxy)-3-aminobenzonitrile (0.62 g, 63%) following general procedure B. N-[5-Cyano-2-(2-methoxyphenoxy)-phenyl]-N′-(thiazol-2-yl)urea (130 mg, 71%) was prepared from 4-(2-methoxyphenoxy)-3-aminobenzonitrile (120 mg, 0.5 mmol) and 2-aminothiazole (60 mg, 0.6 mmol) following general procedure D.

Sources & evidence

ORD record
ord-05647d3d2c1b4e299db8cfc8666dba7b
Source dataset
uspto-grants-2015_09
Patent number
USRE045670E1

Reaction notes

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