2-Aminothiazole → HCID 66998954, compound

HRID 559864Notes

Reaction equation

HRID 559864 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]([Cl:12])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]=1[OH:13].F[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[N+:21]([O-:23])=[O:22].[Cl:24][C:25]1[CH:34]=[C:33]([Cl:35])[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[C:26]=1[O:36][C:37]1[CH:43]=[CH:42][CH:41]=[CH:40][C:38]=1[NH2:39].[NH2:44][C:45]1[S:46][CH:47]=[CH:48][N:49]=1>>[Cl:1][C:2]1[CH:11]=[C:10]([Cl:12])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]=1[O:13][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[N+:21]([O-:23])=[O:22].[Cl:24][C:25]1[CH:34]=[C:33]([Cl:35])[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[C:26]=1[O:36][C:37]1[CH:43]=[CH:42][CH:41]=[CH:40][C:38]=1[NH:39][C:3]([NH:44][C:45]1[S:46][CH:47]=[CH:48][N:49]=1)=[O:13]

Participants

6

Reactant 4

HCID 21552-AminothiazoleHCID 163132,4-Dichloro-1-naphtholHCID 738951-Fluoro-2-nitrobenzeneHCID 66999034HCID 66999034, compound2×

Product 2

HCID 59733155HCID 59733155, compoundYield 40%HCID 66998954HCID 66998954, compoundYield 60%

Procedure

2-(2,4-Dichloronaphth-1-oxy)-1-nitrobenzene (1.17 g, 60%) was prepared from 2,4-dichloronaphth-1-ol (1.06 g, 5.0 mmol) and 1-fluoro-2-nitrobenzene (0.71 g, 5.0 mmol) following the general procedure A. This was reduced to 2-(2,4-dichloronaphth-1-oxy)aniline (0.45 g, 60%, 2.5 mmol scale) following general procedure B. N-[2-(2,4-Dichloronaphth-1-oxy)phenyl]-N′-thiazolylurea (172 g, 40%) was prepared from 2-(2,4-dichloronaphth-1-oxy)aniline (303 mg, 1.0 mmol) and 2-aminothiazole (100 mg, 1.0 mmol) following the general procedure D.

Sources & evidence

ORD record
ord-dd0617dae40848049373d8534be65718
Source dataset
uspto-grants-2011_11
Patent number
US08063081B2

Reaction notes

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