Water → HCID 21438996, compound

HRID 329201Notes

Reaction equation

HRID 329201 reaction equation
C([NH:6][C:7](=[S:11])[S:8][CH2:9][CH3:10])(OCC)=O.[CH3:12][O-:13].[K+].Cl[CH2:16][C:17]#[N:18].O>CO.[I-].[K+]>[CH2:9]([S:8][C:7]1[S:11][C:16]([C:17]#[N:18])=[C:12]([OH:13])[N:6]=1)[CH3:10]

Participants

7

Reactant 4

HCID 962WaterHCID 7856ChloroacetonitrileHCID 21438967HCID 21438967, compoundHCID 23664618Potassium methoxide2×

Product 1

HCID 21438996HCID 21438996, compoundYield 37.8%

Reagents, catalysts & solvents 2

HCID 4875Potassium IodideCatalystHCID 887MethanolSolvent

Procedure

A suspension of 40 g of ethyl N-carbethoxy-dithiocarbamate, 14 g of potassium methylate, 15 g of chloroacetonitrile and 1 g of potassium iodide in 250 ml of methanol was stirred for 3 hours at room temperature under an inert atmosphere and then 14 g of potassium methylate were added. The reaction mixture was refluxed for one hour and water was then added thereto. The aqueous phase was washed with ethyl acetate and then acidified with concentrated hydrochloric acid. The aqueous phase was extracted with ethyl acetate and the extracts were dried, filtered and evaporated to dryness. The residue was empasted with isopropyl ether and then filtered to obtain 14 g of 2-ethylthio-4-hydroxy-5-cyano-thiazole in the form of cream crystals melting at 160° C.

Workup

  1. temperatureThe reaction mixture was refluxed for one hour
  2. washThe aqueous phase was washed with ethyl acetate
  3. extractionThe aqueous phase was extracted with ethyl acetate
  4. customthe extracts were dried
  5. filtrationfiltered
  6. customevaporated to dryness
  7. filtrationfiltered

Sources & evidence

ORD record
ord-90e179088b2542f0a9c64c08e0689529
Source dataset
uspto-grants-1977_04
Patent number
US04020076

Reaction notes

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