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

HRID 924640Notes

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].C(N(CC)CC)C>CN(C)C=O>[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

Conditions

Temperature: 105 °C

Procedure

To a 3 necked 500 ml round bottom flask fitted with a thermometer and a condenser was added 3,7-dinitro-10H-phenothiazine (MW 289.27 g/mol, 29.00 g, 100 mmol), dimethylformamide (58 ml), acetic anhydride (MW 102.09 g/mol, 102.09 g, 1000 mmol) and triethylamine (MW 101.19 g/mol, 40.88 g, 401 mmol). The mixture was heated to 105° C. and stirred at this temperature for 3 hours. The mixture was cooled to ambient temperature (21° C.) before being cooled to 5° C. whereby it was stirred for 1 hour. The product was isolated by filtration and washed with methanol (3×30 ml) to give a light yellow crystalline solid, which was dried at 50° C. for 15 hours (MW 331.31 g/mol, 26.94 g, 81%).

Workup

customTo a 3 necked 500 ml round bottom flask fitted with a thermometer and a condenser
temperatureThe mixture was cooled to ambient temperature (21° C.)
temperaturebefore being cooled to 5° C. whereby it
stirringwas stirred for 1 hour
customThe product was isolated by filtration
washwashed with methanol (3×30 ml)
customto give a light yellow crystalline solid, which
customwas dried at 50° C. for 15 hours (MW 331.31 g/mol, 26.94 g, 81%)

Sources & evidence

ORD record: ord-6a8c37590a334d7f8955bcf7b20714d2
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09283230B2

Reaction notes

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