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

HRID 2300590Notes

Reaction equation

HRID 2300590 reaction equation
[C:1]([NH2:9])(=[S:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[CH:11]([CH3:19])[C:12](=O)[CH2:13][C:14]([O:16][CH3:17])=[O:15].CCOC(C)=O.O>C1(C)C=CC=CC=1>[CH3:17][O:16][C:14](=[O:15])[CH2:13][C:12]1[N:9]=[C:1]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[S:8][C:11]=1[CH3:19]

Participants

5

Reactant 3

HCID 683563ThiobenzamideHCID 9815681Methyl 4-bromo-3-oxopentanoateHCID 22728543Water ethylacetate

Product 1

HCID 2775646methyl 2-(5-methyl-2-phenyl-1,3-thiazol-4-yl)acetate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 13.13 g (95.7 mmol) of thiobenzamide and 5.0 g (23.9 mmol) of methyl 4-bromo-3-oxo-pentanoate in 25 mL of dry toluene was heated at 90° C. for 5 h. The solution was poured into EtOAc/water and the aqueous phase extracted with EtOAc. The organics were washed with brine, dried (MgSO4), filtered, and concentrated. The crude oil was purified by silica gel chromatography eluting with hexanes/EtOAc (3/1 to 2/1) to afford 4.14 g (70%) yield) of the title compound as a pale orange-colored oil: 1H NMR (CDCl3, 400 MHz) δ7.97 (m, 2H), 7.11 (m, 2H), 3.73 (s, 3H), 3.56 (s, 2H), 2.36 (s, 3H).

Workup

  1. extractionthe aqueous phase extracted with EtOAc
  2. washThe organics were washed with brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude oil was purified by silica gel chromatography
  7. washeluting with hexanes/EtOAc (3/1 to 2/1)
  8. customto afford 4.14 g (70%)

Sources & evidence

ORD record
ord-cf0ac6c23b46432bb0488c8f91d5af47
Source dataset
uspto-grants-2002_12
Patent number
US06498174B1

Reaction notes

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