Chloroacetone → Methyl 3-methyl-4-(4-methylthiazol-2-yl)benzoate

HRID 531255Notes

Reaction equation

HRID 531255 reaction equation
[C:1]([C:4]1[CH:13]=[CH:12][C:7]([C:8]([O:10][CH3:11])=[O:9])=[CH:6][C:5]=1[CH3:14])(=[S:3])[NH2:2].Cl[CH2:16][C:17](=O)[CH3:18]>C(O)C>[CH3:14][C:5]1[CH:6]=[C:7]([CH:12]=[CH:13][C:4]=1[C:1]1[S:3][CH:16]=[C:17]([CH3:18])[N:2]=1)[C:8]([O:10][CH3:11])=[O:9]

Participants

4

Reactant 2

HCID 6571ChloroacetoneHCID 53832239Methyl 4-carbamothioyl-3-methylbenzoate

Product 1

HCID 90009102Methyl 3-methyl-4-(4-methylthiazol-2-yl)benzoateYield 69%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Methyl 4-carbamothioyl-3-methylbenzoate (8.9 g, 42.5 mmol) and chloroacetone (3.94 g, 42.5 mmol) were dissolved in ethanol (50 mL), and refluxed for 12 hours. The solvent was evaporated, and the residue was purified on a silica gel column, eluting with 20%-40% ethyl acetate in hexanes, to get methyl 3-methyl-4-(4-methylthiazol-2-yl)benzoate as white waxy solids (contains some ethyl 3-methyl-4-(4-methylthiazol-2-yl)benzoate) (7.4 g, 69% yield). An aliquot amount of the methyl and ethyl ester mixture was separated for identification purpose.

Workup

  1. temperaturerefluxed for 12 hours
  2. customThe solvent was evaporated
  3. customthe residue was purified on a silica gel column
  4. washeluting with 20%-40% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-b4c1e6ea75344a75bb9667b3ae7fe748
Source dataset
uspto-grants-2016_05
Patent number
US09353101B2

Reaction notes

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