Sodium Cyanide → Ethyl thiazole-4-carboxylate

HRID 2397211Notes

Reaction equation

HRID 2397211 reaction equation
[N+:1]([CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5])#[C-:2].[CH:9](OCC)=[S:10].[C-]#N.[Na+]>C(O)C>[CH2:7]([O:6][C:4]([C:3]1[N:1]=[CH:2][S:10][CH:9]=1)=[O:5])[CH3:8]

Participants

5

Reactant 3

HCID 8929Sodium CyanideHCID 533707Ethyl isocyanoacetateHCID 11073343Methanethioic acid, O-ethyl ester

Product 1

HCID 5003096Ethyl thiazole-4-carboxylateYield 92%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Conditions

Temperature
50 °C

Procedure

A solution of 4.52 g. (0.04 m) of ethyl isocyanoacetate and 3.60 g. (0.04 m) of ethyl thioformate in 15 ml. of absolute ethanol is added dropwise with vigorous stirring to a suspension of 0.25 g. of sodium cyanide in 10 ml. ethanol at 15° C. An exotherm developes during the addition and is moderated with ice-bath cooling. The reaction mixture is warmed at 50° C. for 30 minutes. The solvent is then removed in vacuo and the resulting residue extracted with several portions of hot hexane to give a 92% yield of 4-ethoxycarbonyl thiazole.

Workup

  1. customat 15° C
  2. additionAn exotherm developes during the addition
  3. customis moderated with ice-bath
  4. temperaturecooling
  5. customThe solvent is then removed in vacuo
  6. extractionthe resulting residue extracted with several portions of hot hexane

Sources & evidence

ORD record
ord-33a99da0e1a449ccb8c0685184ff5362
Source dataset
uspto-grants-1977_05
Patent number
US04021438

Reaction notes

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