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

HRID 1473976Notes

Reaction equation

HRID 1473976 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]([NH2:11])=[S:10])[CH:5]=[CH:6][CH:7]=1.Br[CH2:13][C:14](=O)[CH3:15]>CN(C=O)C>[CH3:15][C:14]1[N:11]=[C:9]([NH:8][C:4]2[CH:3]=[C:2]([OH:1])[CH:7]=[CH:6][CH:5]=2)[S:10][CH:13]=1

Participants

4

Reactant 2

HCID 11715BromoacetoneHCID 27593303-hydroxyphenylthiourea

Product 1

HCID 534394803-[(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 3-hydroxyphenylthiourea (100 mg, 0.59 mmol) and bromoacetone (98 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 (74 mg).

Workup

  1. customfor the synthesis of derivatives 6 and 7

Sources & evidence

ORD record
ord-f3df65e12da84198992632aa19e0de3c
Source dataset
uspto-grants-2015_04
Patent number
US09018209B2

Reaction notes

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