Acetyl chloride → HCID 10640617, compound

HRID 235271Notes

Reaction equation

HRID 235271 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[C:5](Cl)(=[O:7])[CH3:6].[CH3:9][C:10]1[CH:15]=[CH:14][C:13]([N:16]2[C:25](=[O:26])[CH:24]=[C: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][C:23]3[C:18]([C:19]=2[CH:29]=1)=[N:17][N:16]([C:13]1[CH:12]=[CH:11][C:10]([CH3:9])=[CH:15][CH:14]=1)[C:25](=[O:26])[CH:24]=3)(=[O:7])[CH3:6]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 10565743HCID 10565743, compound

Product 1

HCID 10640617HCID 10640617, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a suspension of 6.4 g of aluminum chloride in methylene chloride was added 2.3 ml of acetyl chloride under ice-cooling and the mixture was stirred for 10 minutes. A solution of 4.7 g of 5,6-dihydro-2-(4-methylphenyl)thieno-[2,3-h]cinnolin-3(2H)-one in methylene chloride was added thereto, the mixture was stirred at room temperature for 30 minutes and then refluxed for an hour. The mixture was poured into ice-cold water and extracted with chloroform. The extract was washed with water, dried over anhydrous magnesium sulfate and concentrated in vacuo. The residue was chromatographed on a silica gel (SiO2 :100 g) column using chloroform as an eluent. The resulting solid was recrystallized from a mixed solvent of chloroform and methanol to give 3.7 g of 8-acetyl-5,6-dihydro-2-(4-methylphenyl)thieno-[2,3-h]cinnolin-3(2H)-one as a white powder, melting at 240°-242° C.

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred at room temperature for 30 minutes
  3. temperaturerefluxed for an hour
  4. additionThe mixture was poured into ice-cold water
  5. extractionextracted with chloroform
  6. washThe extract was washed with water
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated in vacuo
  9. customThe residue was chromatographed on a silica gel (SiO2 :100 g) column
  10. customThe resulting solid was recrystallized from a mixed solvent of chloroform and methanol

Sources & evidence

ORD record
ord-25bd1f3e70e34e50805c261311023b99
Source dataset
uspto-grants-1997_01
Patent number
US05597918

Reaction notes

Loading…