Diethyl Ether → 12-acetyl-5-hydroxy-12H-benzo[a]phenothiazine

HRID 64962Notes

Reaction equation

HRID 64962 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].[OH:5][C:6]1[CH:19]=[C:18]2[C:9]([NH:10][C:11]3[C:16]([S:17]2)=[CH:15][CH:14]=[CH:13][CH:12]=3)=[C:8]2[CH:20]=[CH:21][CH:22]=[CH:23][C:7]=12.C(OCC)C>CN(C=O)C>[C:1]([N:10]1[C:9]2[C:18](=[CH:19][C:6]([OH:5])=[C:7]3[CH:23]=[CH:22][CH:21]=[CH:20][C:8]3=2)[S:17][C:16]2[C:11]1=[CH:12][CH:13]=[CH:14][CH:15]=2)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 6367Acetyl chlorideHCID 137124785-hydroxy-12H-benzo[a]phenothiazine

Product 1

HCID 1371248512-acetyl-5-hydroxy-12H-benzo[a]phenothiazine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Acetyl chloride (2 ml) was added to a solution of 5-hydroxy-12H-benzo[a]phenothiazine (1) (2.65 gm) in DMF (10 ml) and stirred for 30 minutes. Diethyl ether (100 ml) was added to the reaction mixture followed by ice-water (50 ml). The aqueous layer was decanted and the organic layer containing a solid was evaporated to dryness. The resulting residue was treated with acetone and filtered to afford the title compound.

Workup

  1. customThe aqueous layer was decanted
  2. additionthe organic layer containing a solid
  3. customwas evaporated to dryness
  4. additionThe resulting residue was treated with acetone
  5. filtrationfiltered

Sources & evidence

ORD record
ord-557d7981ff714096a9ff30da1c667084
Source dataset
uspto-grants-1986_09
Patent number
US04611056

Reaction notes

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