Propionyl chloride → HCID 131717641, compound

HRID 373535Notes

Reaction equation

HRID 373535 reaction equation
[C:1]1([N:7]2[C:14](=[O:15])[CH:13]([CH2:16][CH:17]=[CH:18][CH3:19])[C:11](=[O:12])[NH:10][C:8]2=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:20](Cl)(=[O:23])[CH2:21][CH3:22]>N1C=CC=CC=1>[C:1]1([N:7]2[C:14](=[O:15])[C:13]([CH2:16][CH:17]=[CH:18][CH3:19])([C:20](=[O:23])[CH2:21][CH3:22])[C:11](=[O:12])[NH:10][C:8]2=[O:9])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 62324Propionyl chlorideHCID 131717642HCID 131717642, compound

Product 1

HCID 131717641HCID 131717641, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
0 °C

Procedure

A quantity of 1.29 g of 1-phenyl-3-methylallyl-barbituric acid prepared as described in Example Ia) is dissolved in 10 ml of pyridine. 0.52 ml of propionyl chloride is added dropwise to this solution which is cooled at 0° C. The reaction mixture is stirred at approximately 0° C. for 30 minutes and then at room temperature for 3 hours, and is then poured on 50 ml of ice water. After stirring with active carbon and filtering, the filtrate is acidified with conc. hydrochloric acid and extracted with methylene chloride. The organic layer is separated, washed with water, dried and evaporated. The final product is purified by means of column chromatography: silica gel/methylene chloride. The title compound is obtained in a yield of 0.65 g; melting-point 76°-80° C.

Workup

  1. waitat room temperature for 3 hours
  2. stirringAfter stirring with active carbon
  3. filtrationfiltering
  4. extractionextracted with methylene chloride
  5. customThe organic layer is separated
  6. washwashed with water
  7. customdried
  8. customevaporated
  9. customThe final product is purified by means of column chromatography

Sources & evidence

ORD record
ord-17bf1731d3ea426cb2d90a3733bf67e6
Source dataset
uspto-grants-1992_11
Patent number
US05164396

Reaction notes

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