Hydrocarbostyril → 6-(4-Chlorobutyryl)-3,4-dihydrocarbostyril

HRID 1462517Notes

Reaction equation

HRID 1462517 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][C:5](Cl)=[O:6].[Cl-].[Al+3].[Cl-].[Cl-].[NH:12]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH2:16][CH2:15][C:13]1=[O:14]>C(=S)=S>[Cl:1][CH2:2][CH2:3][CH2:4][C:5]([C:19]1[CH:18]=[C:17]2[C:22](=[CH:21][CH:20]=1)[NH:12][C:13](=[O:14])[CH2:15][CH2:16]2)=[O:6]

Participants

5

Reactant 3

HCID 64796HydrocarbostyrilHCID 783704-Chlorobutyryl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 128335166-(4-Chlorobutyryl)-3,4-dihydrocarbostyril

Reagents, catalysts & solvents 1

HCID 6348Carbon DisulfideSolvent2×

Procedure

120 Milliliters of γ-chlorobutyryl chloride and 160 g of pulverized anhydrous aluminium chloride were suspended in 300 ml of carbon disulfide. The suspension was refluxed by heating and another suspension of 29.4 g of 3,4-dihydrocarbostyril in 100 ml of carbon disulfide was added dropwise to the first suspension in 1 hour and the reaction was continued for 4 hours under refluxing condition by heating. After the reaction was completed, the reaction mixture was poured into ice-water and the precipitates thus formed were collected by filtration, washed with water and with ether. Then the washed precipitates were recrystallized from acetone to obtain 25.5 g of 6-(4-chloro-1-oxobutyl)-3,4-dihydrocarbostyril in yellow needle-like crystals. Melting point: 158°-160° C.

Workup

  1. temperatureThe suspension was refluxed
  2. temperatureby heating
  3. additionwas added dropwise to the first suspension in 1 hour
  4. temperatureunder refluxing condition
  5. temperatureby heating
  6. customthe precipitates thus
  7. customformed
  8. filtrationwere collected by filtration
  9. washwashed with water and with ether
  10. customThen the washed precipitates
  11. customwere recrystallized from acetone

Sources & evidence

ORD record
ord-c8eaaec3356743539f49d8ad3b77737e
Source dataset
uspto-grants-1984_07
Patent number
US04460593

Reaction notes

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