Acetic Anhydride → 1-(3,7-dinitro-10h-phenothiazin-10-yl)ethanone

HRID 2092905Notes

Reaction equation

HRID 2092905 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]2[NH:8][C:9]3[C:14]([S:15][C:16]=2[CH:17]=1)=[CH:13][C:12]([N+:18]([O-:20])=[O:19])=[CH:11][CH:10]=3)([O-:3])=[O:2].[C:21](OC(=O)C)(=[O:23])[CH3:22]>N1C=CC=CC=1>[N+:18]([C:12]1[CH:11]=[CH:10][C:9]2[N:8]([C:21](=[O:23])[CH3:22])[C:7]3[C:16]([S:15][C:14]=2[CH:13]=1)=[CH:17][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=3)([O-:20])=[O:19]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 43717973,7-dinitro-10H-phenothiazine

Product 1

HCID 2623651-(3,7-dinitro-10h-phenothiazin-10-yl)ethanoneYield 77%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 3,7-dinitrophenothiazine (MW 289.27, 24.0 g, 82.96 mmol), acetic anhydride (MW 102.09, 151 g, 1.48 mol) and pyridine (100 cm3) was stirred at reflux for 18 hours. The warm solution was then cooled to room temperature and poured carefully over ice water. The precipitate formed was filtered to give the title compound (MW 331.26, 21.14 g, 63.81 mmol, 77%) as a sand coloured solid which was recrystallised from acetone to give light yellow needles.

Workup

  1. temperatureat reflux for 18 hours
  2. customThe precipitate formed
  3. filtrationwas filtered

Sources & evidence

ORD record
ord-756694b910314250bc4733bcd67cf930
Source dataset
uspto-grants-2013_05
Patent number
US08440821B2

Reaction notes

Loading…