Ethyl bromopyruvate → 4-Methyl-2-nitro-phenyl-thiazole-4-carboxylic acid ethyl ester

HRID 227236Notes

Reaction equation

HRID 227236 reaction equation
[CH3:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH2:8])=[S:7])=[C:4]([N+:11]([O-:13])=[O:12])[CH:3]=1.[CH3:14][CH2:15][O:16][C:17]([C:19]([CH2:21]Br)=O)=[O:18]>CCO.CCOC(C)=O>[CH2:15]([O:16][C:17]([C:19]1[N:8]=[C:6]([C:5]2[CH:9]=[CH:10][C:2]([CH3:1])=[CH:3][C:4]=2[N+:11]([O-:13])=[O:12])[S:7][CH:21]=1)=[O:18])[CH3:14]

Participants

5

Reactant 2

HCID 66144Ethyl bromopyruvateHCID 541688084-Methyl-2-nitro-thiobenzamide

Product 1

HCID 866229124-Methyl-2-nitro-phenyl-thiazole-4-carboxylic acid ethyl ester

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

4-Methyl-2-nitro-thio benzamide (60 mgs, 0.30 mmol, prepared as described in compound 5, Step 2, was stirred in 1 mL absolute EtOH at room temperature under N2. Ethyl bromo pyruvate (65 mgs, 0.33 mmol) was added, and the resulting solution was heated to 70° C. for 3 h. The reaction was diluted to 30 mL with EtOAc and washed with saturated NaHCO3, and saturated NaCl. The organic layer was dried over MgSO4, filtered and concentrated to a yellow oil, which was used as is in the next step.

Workup

  1. washwashed with saturated NaHCO3, and saturated NaCl
  2. dry with materialThe organic layer was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated to a yellow oil, which

Sources & evidence

ORD record
ord-0071cf80c814424a9604bf2d5f427a1a
Source dataset
uspto-grants-2009_07
Patent number
US07560462B2

Reaction notes

Loading…