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

HRID 1473977Notes

Reaction equation

HRID 1473977 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]([NH2:12])=[S:11])[CH:5]=[CH:6][C:7]=1[CH3:8].Br[CH2:14][C:15](=O)[CH3:16]>CN(C=O)C>[CH3:8][C:7]1[CH:6]=[CH:5][C:4]([NH:9][C:10]2[S:11][CH:14]=[C:15]([CH3:16])[N:12]=2)=[CH:3][C:2]=1[OH:1]

Participants

4

Reactant 2

HCID 11715BromoacetoneHCID 55276261HCID 55276261, compound

Product 1

HCID 534390562-Methyl-5-[(4-methyl-1,3-thiazol-2-yl)amino]phenolYield 61%

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-methylphenyl)thiourea (100 mg, 0.59 mmol) and bromoacetone (96 mg, 0.71 mmol) in dry DMF (2.4 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 61% yield (79 mg).

Workup

  1. customfor the synthesis of derivatives 6 and 7

Sources & evidence

ORD record
ord-919cefcc11cb4843adc5c0cde4db8834
Source dataset
uspto-grants-2015_04
Patent number
US09018209B2

Reaction notes

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