Guaiacol → N-[2-(2-Methoxyphenoxy)pyridin-3-yl]-N'-(thiazol-2-yl)urea

HRID 131841Notes

Reaction equation

HRID 131841 reaction equation
COC1C=CC=C[C:4]=1[OH:9].BrC1C([N+]([O-])=O)=CC=CN=1.[CH3:20][O:21][C:22]1[CH:35]=[CH:34][CH:33]=[CH:32][C:23]=1[O:24][C:25]1[C:30]([NH2:31])=[CH:29][CH:28]=[CH:27][N:26]=1.[NH2:36][C:37]1[S:38][CH:39]=[CH:40][N:41]=1>>[CH3:20][O:21][C:22]1[CH:35]=[CH:34][CH:33]=[CH:32][C:23]=1[O:24][C:25]1[C:30]([NH:31][C:4]([NH:36][C:37]2[S:38][CH:39]=[CH:40][N:41]=2)=[O:9])=[CH:29][CH:28]=[CH:27][N:26]=1

Participants

5

Reactant 4

HCID 460GuaiacolHCID 21552-AminothiazoleHCID 5550542-Bromo-3-nitropyridineHCID 167892082-(2-Methoxyphenoxy)-3-aminopyridine2×

Product 1

HCID 59733053N-[2-(2-Methoxyphenoxy)pyridin-3-yl]-N'-(thiazol-2-yl)ureaYield 61,336.699%

Procedure

2-(2-Methoxy)phenoxy-3-nitropyridine (0.86 g, 70%) was prepared from 2-methoxyphenol (0.68 g, 5.5 mmol) and 2-bromo-3-nitropyridine (1.05 g, 5.0 mmol) following the general procedure A. This compound was reduced to 2-(2-methoxyphenoxy)-3-aminopyridine (0.49 g, 65%) following general procedure B. N-[2-(2-Methoxyphenoxy)pyridin-3-yl]-N′-(thiazol-2-yl)urea (126 g, 74%) was prepared from 2-(2-methoxyphenoxy)-3-aminopyridine (108 mg, 0.5 mmol) and 2-aminothiazole (60 mg, 0.6 mmol) following the general procedure D.

Sources & evidence

ORD record
ord-1a7790eeca8d45bc88b5ec006ee37963
Source dataset
uspto-grants-2008_06
Patent number
US07384967B2

Reaction notes

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