Bromoacetone → 2-Methoxy-5-[(4-methyl-1,3-thiazol-2-yl)amino]phenol

HRID 1473978Notes

Reaction equation

HRID 1473978 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([NH:10][C:11]([NH2:13])=[S:12])[CH:5]=[CH:6][C:7]=1[O:8][CH3:9].Br[CH2:15][C:16](=O)[CH3:17]>CN(C=O)C>[CH3:9][O:8][C:7]1[CH:6]=[CH:5][C:4]([NH:10][C:11]2[S:12][CH:15]=[C:16]([CH3:17])[N:13]=2)=[CH:3][C:2]=1[OH:1]

Participants

4

Reactant 2

HCID 11715BromoacetoneHCID 55276262HCID 55276262, compound

Product 1

HCID 534390572-Methoxy-5-[(4-methyl-1,3-thiazol-2-yl)amino]phenolYield 26%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Following the general procedure for the synthesis of derivatives 6 and 7, a solution of 1-(3-hydroxy-4-methoxyphenyl)thiourea (100 mg, 0.50 mmol) and bromoacetone (83 mg, 0.60 mmol) in dry DMF (2.0 mL) was heated at 60° C. for 6 h. The title compound was obtained after purification by flash chromatography on silica gel (hexane:EtOAc 6/4) in 26% yield (30 mg).

Workup

  1. customfor the synthesis of derivatives 6 and 7

Sources & evidence

ORD record
ord-68af7d98a7bb4f3fb4c4fd61771b711a
Source dataset
uspto-grants-2015_04
Patent number
US09018209B2

Reaction notes

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