Acetyl chloride → HCID 21527018, compound

HRID 1659093Notes

Reaction equation

HRID 1659093 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]2[NH:6][C:7]3[C:12]([S:13][C:14]=2[CH:15]=1)=[CH:11][CH:10]=[CH:9][CH:8]=3.[C:16](Cl)(=[O:18])[CH3:17]>C1C=CC=CC=1>[C:16]([N:6]1[C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:15][C:14]=2[S:13][C:12]2[C:7]1=[CH:8][CH:9]=[CH:10][CH:11]=2)(=[O:18])[CH3:17]

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 2428383-Fluoro-10H-phenothiazine

Product 1

HCID 21527018HCID 21527018, compoundYield 86.1%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

108 grams of 3-fluorophenothiazine were dissolved in 1 liter of dry benzene. 75 grams of acetyl chloride were then added and the mixture heated under reflux for 4 hours, whereupon the mixture was evaporated. The residue was recrystallized from ethanol and 111 grams of 10-acetyl-3-fluorophenothiazine were obtained. MP: 125° Centigrade. The 111 grams of 10-acetyl-3-fluorophenothiazine were heated under reflux for 2 hours with 160 grams of anhydrous aluminium chloride in 800 milliliters of carbon disulphide. The mixture was cooled, and 70 grams of acetyl chloride were added slowly, whereupon the mixture was heated under reflux for 4 hours. The mixture was poured onto crushed ice and extracted with ether. The ether phase was evaporated, the residue dissolved in a mixture of 2 liters of ethanol and 50 milliliters of 50% sodium hydroxide solution and heated for 5 minutes on a steam bath. Thereby 2-acetyl-7-fluorophenothiazine crystallized out as white crystals which melt at 210° Centigrade. Yield: 80 grams.

Workup

  1. temperaturethe mixture heated
  2. temperatureunder reflux for 4 hours, whereupon the mixture
  3. customwas evaporated
  4. customThe residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-a8e140b82c994d45ab90d70913473367
Source dataset
uspto-grants-1976_06
Patent number
US03966930

Reaction notes

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