Acetic Anhydride → 5-acetoxy-12H-benzo[a]phenothiazine

HRID 64960Notes

Reaction equation

HRID 64960 reaction equation
[C:1]([O:4][C:5](=[O:7])[CH3:6])(=O)[CH3:2].OC1[CH:22]=[C:21]2[C:12]([NH:13][C:14]3[C:19]([S:20]2)=[CH:18][CH:17]=[CH:16][CH:15]=3)=[C:11]2C=[CH:24][CH:25]=[CH:26][C:10]=12>N1C=CC=CC=1>[C:5]([O:4][C:1]1[CH:22]=[C:21]2[C:12]([NH:13][C:14]3[C:19]([S:20]2)=[CH:18][CH:17]=[CH:16][CH:15]=3)=[C:11]2[CH:10]=[CH:26][CH:25]=[CH:24][C:2]=12)(=[O:7])[CH3:6]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 137124785-hydroxy-12H-benzo[a]phenothiazine

Product 1

HCID 137124795-acetoxy-12H-benzo[a]phenothiazine

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Acetic anhydride (2 ml) was added to a solution of 5-hydroxy-12H-benzo[a]phenothiazine (1) (1.4 gm) in pyridine (10 ml) and stirred for 15 minutes. The reaction mixture was concentrated under vacuum and ice-water was added to the residue. The resulting precipitate was filtered, air-dried and washed with ethyl acetate to afford the title compound.

Workup

  1. concentrationThe reaction mixture was concentrated under vacuum and ice-water
  2. additionwas added to the residue
  3. filtrationThe resulting precipitate was filtered
  4. customair-dried
  5. washwashed with ethyl acetate

Sources & evidence

ORD record
ord-f74f7076b2d34d5686fe0103fe01206f
Source dataset
uspto-grants-1986_09
Patent number
US04611056

Reaction notes

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