Bromopyruvic Acid → 2-(Cyanomethyl)-1,3-thiazole-4-carboxylic acid

HRID 872752Notes

Reaction equation

HRID 872752 reaction equation
[C:1]([CH2:3][C:4]([NH2:6])=[S:5])#[N:2].Br[CH2:8][C:9](=O)[C:10]([OH:12])=[O:11]>C1COCC1>[C:1]([CH2:3][C:4]1[S:5][CH:8]=[C:9]([C:10]([OH:12])=[O:11])[N:6]=1)#[N:2]

Participants

4

Reactant 2

HCID 70684Bromopyruvic AcidHCID 14162772-Cyanoethanethioamide

Product 1

HCID 431403362-(Cyanomethyl)-1,3-thiazole-4-carboxylic acidYield 48.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

(Cyano)thioacetamide (2 g, 19.97 mmol) was stirred in excess THF (40 mL) under nitrogen atmosphere. The solution was cooled to 0° C. and the solution of 3-bromopyruvic acid (3.33 g, 19.97 mmol) dissolved in 5 mL THF was added dropwise. The mixture was refluxed for 3 h. Solvent was evaporated and the crude product was purified by flash chromatography (silica, eluent: 0-40% DCM-10% MeOH/DCM mixture) to yield 1.615 g of the title compound. 1H NMR (400 MHz; CDCl3): δ 4.20 (s, 2H), 8.33 (s, 1H).

Workup

  1. additionwas added dropwise
  2. temperatureThe mixture was refluxed for 3 h
  3. customSolvent was evaporated
  4. customthe crude product was purified by flash chromatography (silica, eluent: 0-40% DCM-10% MeOH/DCM mixture)

Sources & evidence

ORD record
ord-82f1aebca0114e8a9a6220556b768d37
Source dataset
uspto-grants-2015_03
Patent number
US08975254B2

Reaction notes

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