Acetyl chloride → HCID 23353988, compound

HRID 235267Notes

Reaction equation

HRID 235267 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[C:5](Cl)(=[O:7])[CH3:6].[Cl:9][C:10]1[CH:15]=[CH:14][C:13]([N:16]2[C:25](=[O:26])[CH2:24][CH:23]3[C:18]([C:19]4[CH:29]=[CH:28][S:27][C:20]=4[CH2:21][CH2:22]3)=[N:17]2)=[CH:12][CH:11]=1>C(Cl)Cl>[C:5]([C:28]1[S:27][C:20]2[CH2:21][CH2:22][CH:23]3[C:18]([C:19]=2[CH:29]=1)=[N:17][N:16]([C:13]1[CH:14]=[CH:15][C:10]([Cl:9])=[CH:11][CH:12]=1)[C:25](=[O:26])[CH2:24]3)(=[O:7])[CH3:6]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 10591541HCID 10591541, compound

Product 1

HCID 23353988HCID 23353988, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of 5.7 g of aluminum chloride in 100 ml of methylene chloride was added 2.0 ml of acetyl chloride under ice-cooling and the mixture was stirred at room temperature for 10 minutes. 4.5 g of 2-(4-chlorophenyl)-4,4a,5,6-tetrahydrothieno-[2,3-h]cinnolin-3(2H)-one was added under ice-cooling, and the mixture was refluxed for 2 hours. After cooling, the mixture was poured into ice-cold water and extracted with chloroform. The extract was washed with water, dried over anhydrous magnesium sulfate and the solvent was concentrated in vacuo. The resulting crystal was recrystallized from a mixed solvent of chloroform and ethanol to give 4.7 g of 8-acetyl-2-(4-chlorophenyl)-4,4a,5,6tetrahydrothieno-[2,3-h]cinnolin-3(2H)-one as a white crystal, melting at 155°-157° C.

Workup

  1. temperaturecooling
  2. temperaturecooling
  3. temperaturethe mixture was refluxed for 2 hours
  4. temperatureAfter cooling
  5. additionthe mixture was poured into ice-cold water
  6. extractionextracted with chloroform
  7. washThe extract was washed with water
  8. dry with materialdried over anhydrous magnesium sulfate
  9. concentrationthe solvent was concentrated in vacuo
  10. customThe resulting crystal was recrystallized from a mixed solvent of chloroform and ethanol

Sources & evidence

ORD record
ord-0d243792fffd42e489a4169594666a99
Source dataset
uspto-grants-1997_01
Patent number
US05597918

Reaction notes

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