Iodine → 1-(Butan-2-yl)-phenothiazin-5-ium iodide
Reaction equation
[CH:1]([C:5]1[C:18]2[NH:17][C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[S:10][C:9]=2[CH:8]=[CH:7][CH:6]=1)([CH2:3][CH3:4])[CH3:2].[I:19]I>C(Cl)(Cl)Cl>[I-:19].[CH3:2][CH:1]([C:5]1[C:18]2[C:9](=[S+:10][C:11]3[C:16]([N:17]=2)=[CH:15][CH:14]=[CH:13][CH:12]=3)[CH:8]=[CH:7][CH:6]=1)[CH2:3][CH3:4]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 5 °C
Procedure
The stirred solution of 2-chlorophenothiazine (5.02 g, 21.54 mmol) in anhydrous THF (50 mL) was cooled to −78° C. and under argon sec-butyl lithium (77 mL, 108 mmol) was added drop-wise. After all the addition, the resulting orange mixture was stirred at −78° C. for 3 h, then was allowed to warm to room temperature. The reaction was quenched by the slow addition of saturated ammonium chloride, extracted with ethyl acetate (2×400 mL). The combined organics were washed with brine, dried (MgSO4), filtered, concentrated, and purified by chromatography, using ethyl acetate-hexane gradient to afford 1-sec-butyl-10H-phenothiazine. MS (m/z): [M+H]+=256. To the solution of 1-sec-butyl-10H-phenothiazine (1.0 g, 4.14 mmols) in chloroform (30 mL), at 5° C. was added the solution of iodine (3.2 g, 12.61 mmol) in chloroform (125 mL) drop-wise. After the addition the resulting dark mixture was stirred at 5° C. overnight. Product was filtered, washed several times with chloroform, dried to afford the title compound (1.8 g, 68%).
Workup
- additionAfter the addition the resulting dark mixture
- filtrationProduct was filtered
- washwashed several times with chloroform
- customdried
Sources & evidence
- ORD record
- ord-4dec64e1869b4959ba52e817bf87ddd2
- Source dataset
- uspto-grants-2014_09
- Patent number
- US08828986B2
Reaction notes
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