Chloroacetonitrile → HCID 21438981, compound

HRID 329196Notes

Reaction equation

HRID 329196 reaction equation
[K].[C:2]([NH:7][C:8](=[S:14])[O:9][CH2:10][CH2:11][CH2:12][CH3:13])([O:4]CC)=O.Cl[CH2:16][C:17]#[N:18].C[O-].[K+]>CO>[CH2:10]([O:9][C:8]1[S:14][C:16]([C:17]#[N:18])=[C:2]([OH:4])[N:7]=1)[CH2:11][CH2:12][CH3:13]

Participants

6

Reactant 4

HCID 7856ChloroacetonitrileHCID 5462222PotassiumHCID 20208157HCID 20208157, compoundHCID 23664618Potassium methoxide

Product 1

HCID 21438981HCID 21438981, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 35 g of the potassium salt of n-butyl N-carbethoxy-thiocarbamate, 500 ml of methanol and 7.7 ml of chloroacetonitrile was stirred for 5 hours and then 10.1 g of potassium methylate were added thereto. The reaction mixture was refluxed for 16 hours and was then evaporated to dryness. The residue was dissolved in water and the aqueous phase was washed with ether and then acidified. The acid aqueous phase was extracted with ether and the ether phase was evaporated to dryness to obtain 16 g of 2-n-butoxy-4-hydroxy-5-cyano-thiazole in the form of beige crystals melting at 80° C.

Workup

  1. temperatureThe reaction mixture was refluxed for 16 hours
  2. customwas then evaporated to dryness
  3. dissolutionThe residue was dissolved in water
  4. washthe aqueous phase was washed with ether
  5. extractionThe acid aqueous phase was extracted with ether
  6. customthe ether phase was evaporated to dryness

Sources & evidence

ORD record
ord-ef8ebd83e98142779861d7672c196025
Source dataset
uspto-grants-1977_04
Patent number
US04020076

Reaction notes

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