Phosphorus oxychloride → HCID 18953864, compound

HRID 2379807Notes

Reaction equation

HRID 2379807 reaction equation
P(Cl)(Cl)(Cl)=O.[C:6]([C:9]1[N:10]=[C:11]([C:14]([NH2:16])=O)[S:12][CH:13]=1)(=[O:8])[CH3:7]>CN(C)C=O>[C:6]([C:9]1[N:10]=[C:11]([C:14]#[N:16])[S:12][CH:13]=1)(=[O:8])[CH3:7]

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 18953789HCID 18953789, compound

Product 1

HCID 18953864HCID 18953864, compoundYield 74.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Phosphorus oxychloride (8.5 ml) was added slowly to a solution of 4-acetyl-2-thiazolecarboxamide (10.0 g) in N,N-dimethylformamide (500 ml) at 0°-5° C. with cooling on an ice-water bath. The mixture was stirred at 0°-5° C. with cooling on an ice-water bath for 4 hours and then was poured into ice water (400 ml). The solution was extracted with ethyl acetate (750 ml×2). The extract was dried with magnesium sulfate. The solvent was removed under reduced pressure and the residue was crystallized from water to afford 4-acetyl-2-cyanothiazole (6.7 g).

Workup

  1. temperaturewith cooling on an ice-water bath
  2. temperaturewith cooling on an ice-water bath for 4 hours
  3. extractionThe solution was extracted with ethyl acetate (750 ml×2)
  4. dry with materialThe extract was dried with magnesium sulfate
  5. customThe solvent was removed under reduced pressure
  6. customthe residue was crystallized from water

Sources & evidence

ORD record
ord-a307b69eee014fd9a6cf6a79300b6745
Source dataset
uspto-grants-1994_11
Patent number
US05364871

Reaction notes

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