Thioacetamide → HCID 178468666, compound

HRID 129833Notes

Reaction equation

HRID 129833 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:10]=[C:9]([C:11](=O)[CH2:12]Br)[NH:8][N:7]=1)=[O:5])[CH3:2].[C:15]([NH2:18])(=[S:17])[CH3:16]>C(O)C>[CH2:1]([O:3][C:4]([C:6]1[CH:10]=[C:9]([C:11]2[N:18]=[C:15]([CH3:16])[S:17][CH:12]=2)[NH:8][N:7]=1)=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 2723949ThioacetamideHCID 1784690765-(2-Bromoacetyl)pyrazole-3-carboxylic acid ethyl ester

Product 1

HCID 178468666HCID 178468666, compoundYield 71.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 5-(2-bromoacetyl)pyrazole-3-carboxylic acid ethyl ester (5.30 g), thioacetamide (1.60 g), and ethanol (100 ml) was stirred at 60° C. for 30 minutes and concentrated. The residue was dissolved in 50 ml of 2N HCl solution, and washed with ethyl ether (2×50 ml). The aqueous solution was separated and neutralized with solid NaHCO3. The mixture was then extracted with ethyl acetate (233 100 ml). The ethyl acetate solution was dried over sodium sulfate and concentrated to afford 3.46 g of 5-(2-methylthiazol-4-yl)pyrazole-3-carboxylic acid ethyl ester as pale yellow solids, mp 141-142° C. NMR: 1.41 (t, 3H), 2.78 (s, 3H, thiazolyl methyl), 4.42 (q, 2H), 7.15 (s, 1H, thiazolyl H), 7.47 (s, 1H, 4-pyrazolyl H).

Workup

  1. concentrationconcentrated
  2. dissolutionThe residue was dissolved in 50 ml of 2N HCl solution
  3. washwashed with ethyl ether (2×50 ml)
  4. customThe aqueous solution was separated
  5. extractionThe mixture was then extracted with ethyl acetate (233 100 ml)
  6. dry with materialThe ethyl acetate solution was dried over sodium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-f53de928ac4d4bb09fafc71500646b32
Source dataset
uspto-grants-1995_11
Patent number
US05470862

Reaction notes

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