Chloroacetyl chloride → HCID 11107745, compound

HRID 232704Notes

Reaction equation

HRID 232704 reaction equation
[Cl:1][CH2:2][C:3](Cl)=[O:4].[Cl-].[Al+3].[Cl-].[Cl-].[CH2:10]([C:12]1[CH:13]=[CH:14][CH:15]=[C:16]2[C:21]=1[NH:20][C:19](=[O:22])[CH:18]=[CH:17]2)[CH3:11]>C(=S)=S>[Cl:1][CH2:2][C:3]([C:14]1[CH:15]=[C:16]2[C:21](=[C:12]([CH2:10][CH3:11])[CH:13]=1)[NH:20][C:19](=[O:22])[CH:18]=[CH:17]2)=[O:4]

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 108668132(1H)-Quinolinone, 8-ethyl-

Product 1

HCID 11107745HCID 11107745, compound

Reagents, catalysts & solvents 1

HCID 6348Carbon DisulfideSolvent

Procedure

To a solution of 62 ml of chloroacetyl chloride in 600 ml of carbon disulfide were added, with ice-cooling, 173 g of aluminum chloride and 44 g of 8-ethylcarbostyril in this order. The mixture was refluxed for 6 hours. The reaction mixture was subjected to distillation to remove carbon disulfide. The residue was poured into ice water. The mixture was stirred at room temperature overnight. The insoluble portion was collected by filtration, washed with water and dried to obtain 55 g of 6-chloroacetyl-8-ethylcarbostyril as a brown powder.

Workup

  1. temperaturecooling
  2. temperatureThe mixture was refluxed for 6 hours
  3. distillationThe reaction mixture was subjected to distillation
  4. customto remove carbon disulfide
  5. additionThe residue was poured into ice water
  6. filtrationThe insoluble portion was collected by filtration
  7. washwashed with water
  8. customdried

Sources & evidence

ORD record
ord-379c6a31a2e94220a350956cae039110
Source dataset
uspto-grants-1997_01
Patent number
US05591751

Reaction notes

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