Acetic Anhydride → HCID 67214036, compound
Reaction equation
[CH3:1][NH:2][C:3]1[CH:4]=[CH:5][C:6]2[NH:7][C:8]3[C:13]([S:14][C:15]=2[CH:16]=1)=[CH:12][C:11]([NH:17][CH3:18])=[CH:10][CH:9]=3.[C:19](OC(=O)C)(=[O:21])[CH3:20]>N1C=CC=CC=1>[CH3:1][NH:2][C:3]1[CH:4]=[CH:5][C:6]2[N:7]([C:19](=[O:21])[CH3:20])[C:8]3[C:13]([S:14][C:15]=2[CH:16]=1)=[CH:12][C:11]([NH:17][CH3:18])=[CH:10][CH:9]=3Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 100 °C
Procedure
The 3,7-dimethylamino-10H-phenothiazine obtained in Synthesis 7 was placed in a 250 cm3 round bottom flask and acetic anhydride ((H3CCO)2O, 40 cm3) and pyridine (10 cm3) were added, and the resulting solution was heated at 100° C. for 18 hours with stirring. The reaction mixture was cooled to room temperature and then poured carefully into ice-water while stirring to give a light brown solid, which was filtered using a standard Buchner funnel apparatus with a water aspirator, washed once with water (100 cm3), and dried in an oven at 60° C. for 3 hours to yield the title compound, which was recrystallised from ethanol by dissolving it in hot ethanol (100 cm3), adding activated charcoal (1 g), filtering to remove the charcoal, cooling the solution to 5° C. using an ice-water bath so that a precipitate formed (colourless crystals), and filtering using a standard Buchner filter with a water aspirator in order to collect the crystals. The crystals where then dried in an oven at 60° C. for 3 hours (MW 327.45, 4.25 g, 13.0 mmol, yield 49%).
Workup
- customwas placed in a 250 cm3 round bottom flask
- temperatureThe reaction mixture was cooled to room temperature
- stirringwhile stirring
- customto give a light brown solid, which
- filtrationwas filtered
- washwashed once with water (100 cm3)
- customdried in an oven at 60° C. for 3 hours
Sources & evidence
- ORD record
- ord-d5c61b26a7d94cbb986ed42e046d0dde
- Source dataset
- uspto-grants-2013_05
- Patent number
- US08440821B2
Reaction notes
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