2-Aminothiazole → 4-(2-nitrophenoxy)benzonitrile

HRID 1983234Notes

Reaction equation

HRID 1983234 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([OH:9])=[CH:5][CH:4]=1)#[N:2].F[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[N+:17]([O-:19])=[O:18].[C:20]([C:22]1[CH:35]=[CH:34][C:25]([O:26][C:27]2[CH:33]=[CH:32][CH:31]=[CH:30][C:28]=2[NH2:29])=[CH:24][CH:23]=1)#[N:21].[NH2:36][C:37]1[S:38][CH:39]=[CH:40][N:41]=1>>[C:1]([C:3]1[CH:8]=[CH:7][C:6]([O:9][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[N+:17]([O-:19])=[O:18])=[CH:5][CH:4]=1)#[N:2].[C:20]([C:22]1[CH:35]=[CH:34][C:25]([O:26][C:27]2[CH:33]=[CH:32][CH:31]=[CH:30][C:28]=2[NH:29][C:6]([NH:36][C:37]2[S:38][CH:39]=[CH:40][N:41]=2)=[O:9])=[CH:24][CH:23]=1)#[N:21]

Participants

6

Reactant 4

HCID 21552-AminothiazoleHCID 130194-CyanophenolHCID 738951-Fluoro-2-nitrobenzeneHCID 8156494-(2-aminophenoxy)benzonitrile2×

Product 2

HCID 92134354-(2-nitrophenoxy)benzonitrileYield 69%HCID 59732941HCID 59732941, compoundYield 65%

Procedure

2-(4-Cyanophenoxy)-1-nitrobenzene (0.82 g, 69%) was prepared from 4-cyano-phenol (0.66 g, 5.5 mmol) and 1-fluoro-2-nitrobenzene (0.71 g, 5.0 mmol) following the general procedure A. This was reduced to 2-(4-cyanophenoxy)aniline (0.47 g, 65%) following general procedure B. N-[2-(4-Cyanophenoxy)phenyl]-N′-thiazolylurea (110 mg, 65%) was prepared from 2-(4-cyanophenoxy)aniline (105 mg, 0.5 mmol) and 2-aminothiazole (60 mg, 0.6 mmol) following the general procedure D.

Sources & evidence

ORD record
ord-c906318f7b194b26b5ed7454e03b4b73
Source dataset
uspto-grants-2009_06
Patent number
US07541373B2

Reaction notes

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