Water → 10-acetyl-4-chloro-3-hydroxy-10H-phenothiazine

HRID 979083Notes

Reaction equation

HRID 979083 reaction equation
[Cl:1][C:2]1[C:15]2[S:14][C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[NH:7][C:6]=2[CH:5]=[CH:4][C:3]=1[OH:16].[C:17](Cl)(=[O:19])[CH3:18].C(OCC)(=O)C.O>CN(C=O)C>[C:17]([N:7]1[C:6]2[CH:5]=[CH:4][C:3]([OH:16])=[C:2]([Cl:1])[C:15]=2[S:14][C:13]2[C:8]1=[CH:9][CH:10]=[CH:11][CH:12]=2)(=[O:19])[CH3:18]

Participants

6

Reactant 4

HCID 962WaterHCID 6367Acetyl chlorideHCID 8857Ethyl AcetateHCID 98814184-chloro-3-hydroxy-10H-phenothiazine

Product 1

HCID 1388203310-acetyl-4-chloro-3-hydroxy-10H-phenothiazine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-chloro-3-hydroxyphenothiazine (2.2 g) in DMF (10 ml) was added 10 ml of acetyl chloride. The reaction mixture was stirred at ambient temperature for 1 hour. Ethyl acetate was then added, followed by ice and H2O. The organic layer was separated, dried and evaporated. The resulting residue was purified by chromatography on silica gel to give 1.4 g of 10-acetyl-4-chloro-3-hydroxy-10H-phenothiazine (m.p. 214° C.).

Workup

  1. customThe organic layer was separated
  2. customdried
  3. customevaporated
  4. customThe resulting residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-538072a4fc7c40ada44760109d8539a9
Source dataset
uspto-grants-1987_05
Patent number
US04666907

Reaction notes

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