Dimethylformamide → 3-acetoxy-10-acetyl-4-chloro-10H-phenothiazine

HRID 979082Notes

Reaction equation

HRID 979082 reaction equation
[C:1]([O:4][C:5]1[CH:6]=[CH:7][C:8]2[NH:9][C:10]3[C:15]([S:16][C:17]=2[C:18]=1[Cl:19])=[CH:14][CH:13]=[CH:12][CH:11]=3)(=[O:3])[CH3:2].[C:20](Cl)(=[O:22])[CH3:21].CN(C=O)C.CC(C)([O-])C.[K+]>O>[C:1]([O:4][C:5]1[CH:6]=[CH:7][C:8]2[N:9]([C:20](=[O:22])[CH3:21])[C:10]3[C:15]([S:16][C:17]=2[C:18]=1[Cl:19])=[CH:14][CH:13]=[CH:12][CH:11]=3)(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6367Acetyl chlorideHCID 138820263-acetoxy-4-chloro-10H-phenothiazineHCID 23665647Potassium tert-butoxide

Product 1

HCID 138820323-acetoxy-10-acetyl-4-chloro-10H-phenothiazine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 1.1 g of 3-acetoxy-4-chloro-10H-phenothiazine (see Example 4) was added acetyl chloride (7 ml), DMF (5 ml) and potassium tert-butoxide (0.42 g). The reaction mixture was stirred at ambient temperature for 1 hour and then, poured in water. The resulting precipitate was filtered and purified by chromatography on silica gel to give (1.08 g) 3-acetoxy-10-acetyl-4-chloro-10H-phenothiazine (m.p. 155° C.).

Workup

  1. filtrationThe resulting precipitate was filtered
  2. custompurified by chromatography on silica gel

Sources & evidence

ORD record
ord-c9c006496aa34893a501b9f853e62abb
Source dataset
uspto-grants-1987_05
Patent number
US04666907

Reaction notes

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