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

HRID 231043Notes

Reaction equation

HRID 231043 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-e422749e714e492081fd94dafe2a4152
Source dataset
uspto-grants-1989_07
Patent number
US04845083

Reaction notes

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