Pyridine → 3-acetoxy-4-chloro-10H-phenothiazine

HRID 979077Notes

Reaction equation

HRID 979077 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].N1C=CC=CC=1.[C:23](OC(=O)C)(=[O:25])[CH3:24]>O>[C:23]([O:16][C:3]1[CH:4]=[CH:5][C:6]2[NH:7][C:8]3[C:13]([S:14][C:15]=2[C:2]=1[Cl:1])=[CH:12][CH:11]=[CH:10][CH:9]=3)(=[O:25])[CH3:24]

Participants

5

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 98814184-chloro-3-hydroxy-10H-phenothiazine

Product 1

HCID 138820263-acetoxy-4-chloro-10H-phenothiazine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 1.8 g of 4-chloro-3-hydroxy-10H-phenothiazine (see Example 3) in 20 ml of acetic anhydride was added 1.2 ml of pyridine. The reaction mixture was then stirred at ambient temperature for 12 hours and then poured in water (75 ml). The resulting precipitate was filtered, washed with water and dried under vacuum to give 1.65 g of 3-acetoxy-4-chloro-10H-phenothiazine (m.p.: 173° C.).

Workup

  1. filtrationThe resulting precipitate was filtered
  2. washwashed with water
  3. customdried under vacuum

Sources & evidence

ORD record
ord-cb567120926741889985944c73776cac
Source dataset
uspto-grants-1987_05
Patent number
US04666907

Reaction notes

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