Thiobenzamide → methyl 2-(5-methyl-2-phenyl-1,3-thiazol-4-yl)acetate

HRID 1597456Notes

Reaction equation

HRID 1597456 reaction equation
Br[CH:2]([CH3:10])[C:3](=O)[CH2:4][C:5]([O:7][CH3:8])=[O:6].[C:11]([NH2:19])(=[S:18])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>>[CH3:8][O:7][C:5](=[O:6])[CH2:4][C:3]1[N:19]=[C:11]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[S:18][C:2]=1[CH3:10]

Participants

3

Reactant 2

HCID 683563ThiobenzamideHCID 9815681Methyl 4-bromo-3-oxopentanoate

Product 1

HCID 2775646methyl 2-(5-methyl-2-phenyl-1,3-thiazol-4-yl)acetateYield 70%

Procedure

The title compound (827 mg) was prepared from 1.0 g (4.78 mmol) of methyl 4-bromo-3-oxo-pentanoate and 2.6 g (19.14 mmol) of thiobenzamide according to the method of Intermediate 42 followed by purification via silica gel flash column chromatography using hexanes/EtOAc (3:1) as eluent: low resolution MS (ES) m/e 270 (MNa+), 248 (MH+).

Workup

  1. customfollowed by purification via silica gel flash column chromatography

Sources & evidence

ORD record
ord-5af55ae040cc422984d1a6005fb07c28
Source dataset
uspto-grants-2001_09
Patent number
US06294580B1

Reaction notes

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