Benzyl Chloride → HCID 19816144, compound
Reaction equation
[C:1]([CH2:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([CH2:13][S:14]([NH:17][CH3:18])(=[O:16])=[O:15])[CH:11]=2)[NH:6][CH:5]=1)#[N:2].[H-].[Na+].[CH2:21](Cl)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>CN(C)C=O>[C:1]([CH2:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([CH2:13][S:14]([NH:17][CH3:18])(=[O:16])=[O:15])[CH:11]=2)[N:6]([CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:5]=1)#[N:2]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -30 °C
Procedure
3-(Cyanomethyl)-N-methyl-1H-indole-5-methanesulphonamide (0.4 g) was dissolved in re-distilled dimethylformamide (10 ml) and treated with sodium hydride (0.132 g, 80% dispersion in oil). After 0.5 h the stirred suspension was cooled to -30° C. and treated with distilled benzyl chloride (0.19 g). The mixture was allowed to warm to 10°, stirred for 1 h and then poured onto ice (10 g). The suspension was filtered, and the solid collected and washed with water (20 ml) and cyclohexane (30 ml). The solid was purified by chromatography (M) and the appropriate fractions were combined and concentrated in vacuo to 20 ml, whereupon a solid crystallised out which was collected and dried to give the title compound (0.12 g), m.p. 133°-135°. T.l.c. (M), Rf 0.4, (KMnO4)
Workup
- temperatureto warm to 10°
- additionpoured onto ice (10 g)
- filtrationThe suspension was filtered
- customthe solid collected
- washwashed with water (20 ml) and cyclohexane (30 ml)
- customThe solid was purified by chromatography (M)
- concentrationconcentrated in vacuo to 20 ml, whereupon a solid
- customcrystallised out which
- customwas collected
- customdried
Sources & evidence
- ORD record
- ord-9ada6d10694d44f2a8817e46beb52958
- Source dataset
- uspto-grants-1991_08
- Patent number
- US05037845
Reaction notes
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