Chloroacetyl chloride → HCID 14627530, compound

HRID 1708366Notes

Reaction equation

HRID 1708366 reaction equation
[NH2:1][C:2]1[C:3](=[O:13])[NH:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][C:6]=2[CH3:12].C(N(CC)CC)C.[Cl:21][CH2:22][C:23](Cl)=[O:24]>ClCCl.CC(C)=O>[Cl:21][CH2:22][C:23]([NH:1][C:2]1[C:3](=[O:13])[NH:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][C:6]=2[CH3:12])=[O:24]

Participants

6

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 8471TriethylamineHCID 14627529HCID 14627529, compound

Product 1

HCID 14627530HCID 14627530, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a solution prepared by 2.9 g of 3-amino-8-methylcarbostyril, 3.5 ml of triethylamine in 50 ml of dichloromethane was added dropwise a solution prepared by 1.9 ml of chloroacetyl chloride in 10 ml of dichloromethane under ice-cooled condition. After the dropwise addition, the reaction mixture was stirred at room temperature for 30 minutes. Then the reaction mixture was concentrated by removing the solvent by evaporation under reduced pressure, the residue thus obtained was suspended in aceton and the suspension was poured in an ice-water. The crystals formed were collected by filtration, washed with water, dried, then recrystallized from acetone-water to obtain 3.6 g of 3-chloroacetylamino-8-methylcarbostyril. White powdery substance. Melting point: 271.5°-272° C. (decomposed).

Workup

  1. additionwas added dropwise a solution
  2. temperaturecooled condition
  3. additionAfter the dropwise addition
  4. concentrationThen the reaction mixture was concentrated
  5. customby removing the solvent
  6. customby evaporation under reduced pressure
  7. customthe residue thus obtained
  8. customThe crystals formed
  9. filtrationwere collected by filtration
  10. washwashed with water
  11. customdried
  12. customrecrystallized from acetone-water

Sources & evidence

ORD record
ord-b3afac8087b34d62ac1ce20ef237f8d8
Source dataset
uspto-grants-1994_10
Patent number
US05358949

Reaction notes

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