Sodium Cyanide → Ethyl 5-phenylthiazole-4-carboxylate

HRID 915683Notes

Reaction equation

HRID 915683 reaction equation
[C-]#N.[Na+].[N+:4]([CH2:6][C:7]([O:9][CH2:10][CH3:11])=[O:8])#[C-:5].C(O[C:15](=[S:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)C>C(O)C>[CH2:10]([O:9][C:7]([C:6]1[N:4]=[CH:5][S:22][C:15]=1[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:8])[CH3:11]

Participants

5

Reactant 3

HCID 8929Sodium CyanideHCID 533707Ethyl isocyanoacetateHCID 578278Ethyl thiobenzoate

Product 1

HCID 12300673Ethyl 5-phenylthiazole-4-carboxylateYield 62%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Conditions

Temperature
50 °C

Procedure

Prepare a suspension of NaCN (0.25 g, 5.2 mmol) in ethanol (50 mL). Add dropwise ethyl isocyanoacetate (5 mL, 45.6 mmol) and thiobenzoic acid O-ethyl ester (6.9 g, 41.5 mmol) in ethanol (25 mL). Stir the reaction mixture at 50° C. for 96 hours and then concentrate in vacuo to an oil. Chromatograph (silica gel, 3:7 hexane/ethyl acetate) to afford 5-phenylthiazole-4-carboxylic acid ethyl ester (6.0 g). MS: m/e=234 (MH+).

Workup

  1. customPrepare
  2. concentrationconcentrate in vacuo to an oil

Sources & evidence

ORD record
ord-c99bc89b324c413190c1cf1b6f1ef496
Source dataset
uspto-grants-2007_09
Patent number
US07265246B2

Reaction notes

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