Ammonia → 10-(3-Chloropropyl)-2-(trifluoromethyl)-10H-phenothiazine
Reaction equation
N.[Na].[F:3][C:4]([F:20])([F:19])[C:5]1[CH:18]=[CH:17][C:16]2[S:15][C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[NH:8][C:7]=2[CH:6]=1.Br[CH2:22][CH2:23][CH2:24][Cl:25]>CCCCCCC>[Cl:25][CH2:24][CH2:23][CH2:22][N:8]1[C:7]2[CH:6]=[C:5]([C:4]([F:3])([F:19])[F:20])[CH:18]=[CH:17][C:16]=2[S:15][C:14]2[C:9]1=[CH:10][CH:11]=[CH:12][CH:13]=2Participants
Conditions
- Temperature
- -40 °C
Procedure
Into a 5 liter reactor fitted with stirring and cooling means and maintained at about -40° C., there were poured 1 liter of liquid ammonia, 11.5 g (0.5 mole) of metallic sodium, 0.5 g of ferric acetate and then, slowly, 133.5 g (0.5 mole) of 2-trifluoromethyl-phenothiazine. The mixture was stirred for one hour and there were added 78.8 g (0.5 mole) of 1-bromo-3-chloropropane. After stirring for some minutes, the mixture was allowed to warm slowly up to room temperature, with elimination of the liquid ammonia. There were then added 2 liters of heptane and stirring was maintained for 12 hours. The mixture was then refluxed for one hour and filtered, washed with heptane, evaporated to dryness and recrystallized from heptane to give 270 g (yield 81%) of N-(γ-chloropropyl)-2-trifluoromethyl-phenothiazine.
Workup
- customInto a 5 liter reactor fitted
- temperaturecooling means
- stirringThe mixture was stirred for one hour
- stirringAfter stirring for some minutes
- stirringstirring
- temperaturewas maintained for 12 hours
- temperatureThe mixture was then refluxed for one hour
- filtrationfiltered
- washwashed with heptane
- customevaporated to dryness
- customrecrystallized from heptane
Sources & evidence
- ORD record
- ord-469c6b0a16fa48bdac90fcc50979291c
- Source dataset
- uspto-grants-1980_01
- Patent number
- US04183926
Reaction notes
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