2-Bromopropiophenone → 2-Amino-4-phenyl-5-methylthiazole

HRID 2358030Notes

Reaction equation

Br[CH:2]([CH3:11])[C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=O.[NH2:12][C:13]([NH2:15])=[S:14]>>[NH2:15][C:13]1[S:14][C:2]([CH3:11])=[C:3]([C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=2)[N:12]=1

Participants

Reactant 2

HCID 164522-Bromopropiophenone

HCID 2723790Thiourea

Product 1

HCID 961292-Amino-4-phenyl-5-methylthiazole

Procedure

Reaction of a α-substituted-α-bromoacetophenone with thiourea or substituted thiourea, at elevated temperatures may give gave an intermediate G1. Suitably, this reaction may be performed under refluxing conditions in the presence of DMF (dimethylformamide). This intermediate (G1) may be reacted with chlorosulfonic acid to yield the sulfonyl chloride B-1. For example 2-bromopropiophenone may be reacted with thiourea to yield 2-amino-5-methyl-4-phenylthiazole, which can be further transformed to 4-(2-amino-5-methylthiazol-4-yl)phenyl sulfonyl chloride.

Sources & evidence

ORD record: ord-fc63787a9d83469284a279a6c0b45bd9
Source dataset: uspto-grants-2010_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07763641B2

Reaction notes

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