m-Chloroperbenzoic acid → 5-Acetoxy-12H-benzo[a]phenothiazine-7-oxide

HRID 64974Notes

Reaction equation

HRID 64974 reaction equation
[C:1]([O:4][C:5]1[CH:18]=[C:17]2[C:8]([NH:9][C:10]3[C:15]([S:16]2)=[CH:14][CH:13]=[CH:12][CH:11]=3)=[C:7]2[CH:19]=[CH:20][CH:21]=[CH:22][C:6]=12)(=[O:3])[CH3:2].ClC1C=C(C=CC=1)C(OO)=[O:28]>ClCCl.CO>[C:1]([O:4][C:5]1[CH:18]=[C:17]2[C:8]([NH:9][C:10]3[C:15]([S:16]2=[O:28])=[CH:14][CH:13]=[CH:12][CH:11]=3)=[C:7]2[CH:19]=[CH:20][CH:21]=[CH:22][C:6]=12)(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 137124795-acetoxy-12H-benzo[a]phenothiazine

Product 1

HCID 137124815-Acetoxy-12H-benzo[a]phenothiazine-7-oxide

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a suspension of 5-acetoxy-12H-benzo[a]phenothiazine (10 g) in dichloromethane (125 cc) there was rapidly added a solution of 85% m-chloroperoxybenzoic acid (6.61 g) in methanol (125 ml). At first the solids dissolved, then after a few minutes a new solid separated out of solution. After 1 and 1/2 hours the mixture was filtered and the solid washed with dichloromethane. The title compound was thus obtained pure (8.76 g), m.p. 179°-181° C.

Workup

  1. dissolutionAt first the solids dissolved
  2. customafter a few minutes a new solid separated out of solution
  3. filtrationAfter 1 and 1/2 hours the mixture was filtered
  4. washthe solid washed with dichloromethane

Sources & evidence

ORD record
ord-2c7b3196c3f44de2ba26d71b766c4429
Source dataset
uspto-grants-1986_09
Patent number
US04611056

Reaction notes

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