Phenothiazine → Sodium 3-(10H-phenothiazin-10-yl)propane-1-sulfonate
Reaction equation
[H-].[Na+:2].[CH:3]1[C:16]2[NH:15][C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[S:8][C:7]=2[CH:6]=[CH:5][CH:4]=1.[CH2:17]1[CH2:23][S:20](=[O:22])(=[O:21])[O:19][CH2:18]1>O1CCCC1>[CH:13]1[C:14]2[N:15]([CH2:18][CH2:17][CH2:23][S:20]([O-:22])(=[O:21])=[O:19])[C:16]3[C:7](=[CH:6][CH:5]=[CH:4][CH:3]=3)[S:8][C:9]=2[CH:10]=[CH:11][CH:12]=1.[Na+:2]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
A portion of sodium hydride (17.7 g, 0.44 moles) dispersed in mineral oil is first washed with petroleum ether (b.p. 40-60° C.) and then suspended in 200 mL dry tetrahydrofuran, in a 2 L three-neck flask. A solution of phenothiazine (80.0 g, 0.4 moles) dissolved in tetrahydrofuran (400 mL) is added under argon through a cannula. The mixture is shaken, always under argon, for one hour at room temperature and then for 30 minutes at 50° C. The mixture acquires an orange colour, following the formation of the phenothiazine anion. After the suspension has cooled to 0° C., a solution of 1,3-propanesultone (35 mL, 0.4 moles) in tetrahydrofuran is added also through a cannula. The colour of the mixture changes almost immediately to clear yellow. The mixture is stirred at 0° C. for thirty minutes after the addition of the sultone and then at room temperature for another thirty minutes.
Workup
- washis first washed with petroleum ether (b.p. 40-60° C.)
- customsuspended in 200 mL dry tetrahydrofuran, in a 2 L three-neck flask
- additionis added under argon through a cannula
- waitfor 30 minutes at 50° C
- temperatureAfter the suspension has cooled to 0° C.
- stirringThe mixture is stirred at 0° C. for thirty minutes
- waitat room temperature for another thirty minutes
Sources & evidence
- ORD record
- ord-f192627ff625481d92030d7108bd4344
- Source dataset
- uspto-grants-2010_12
- Patent number
- US07855287B2
Reaction notes
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