2-Aminothiazole → HCID 66998954, compound

HRID 2276116Notes

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].NC1C=CC=CC=1.[Cl:31][C:32]1[CH:41]=[C:40]([Cl:42])[C:39]2[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=2)[C:33]=1[O:43][C:44]1[CH:50]=[CH:49][CH:48]=[CH:47][C:45]=1[NH2:46].[NH2:51][C:52]1[S:53][CH:54]=[CH:55][N:56]=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:31][C:32]1[CH:41]=[C:40]([Cl:42])[C:39]2[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=2)[C:33]=1[O:43][C:44]1[CH:50]=[CH:49][CH:48]=[CH:47][C:45]=1[NH:46][C:3]([NH:51][C:52]1[S:53][CH:54]=[CH:55][N:56]=1)=[O:13]

Participants

Reactant 5

HCID 21552-Aminothiazole

HCID 6115Aniline

HCID 163132,4-Dichloro-1-naphthol

HCID 738951-Fluoro-2-nitrobenzene

HCID 66999034HCID 66999034, compound

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-a004a00f22484664a24f9936a069ecf4
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: USRE045670E1

Reaction notes

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