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
- 120 °C
Procedure
The 3,7-dimethylamino-10H-phenothiazine obtained in Synthesis 1 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 120° 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 (MW 327.45, 4.63 g, 14.1 mmol, yield 53%), 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.
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-423c736685e04bbfbbfd2be34993c6a6
- Source dataset
- uspto-grants-2013_05
- Patent number
- US08440821B2
Reaction notes
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