Epichlorohydrin → HCID 13239942, compound

HRID 358423Notes

Reaction equation

HRID 358423 reaction equation
[CH3:1][CH:2]([NH:9][S:10]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[N+:19]([O-:21])=[O:20])(=[O:12])=[O:11])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[H-].[Na+].[CH2:24]([CH:26]1[O:28][CH2:27]1)Cl>>[O:28]1[CH2:27][CH:26]1[CH2:24][N:9]([CH:2]([CH3:1])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1)[S:10]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[N+:19]([O-:21])=[O:20])(=[O:12])=[O:11]

Participants

4

Reactant 3

HCID 7835EpichlorohydrinHCID 24758Sodium hydrideHCID 604309HCID 604309, compound

Product 1

HCID 13239942HCID 13239942, compoundYield 97%

Procedure

2.1 g (6.6 mmol) of N-α-methylbenzyl-2-nitrobenzenesulfonamide was dissolved in 10 ml of epichlorohydrin, to which was gradually added at room temperature 0.35 g (7.3 mmol) of 50% sodium hydride, followed by agitating at room temperature for 30 minutes and reacting under reflux for 1 hour. The epichlorohydrin was distilled off under reduced pressure, water was added and extracted with ethyl acetate. The ethyl acetate phase was dried over anhydrous magnesium sulfate, concentrated, and purified by the silica gel chromatography to obtain the intended product (Compound No. 33). The yield was 97% and the nD26.5 value was 1.5572. The results of the elemental analysis are shown below.

Workup

  1. temperatureunder reflux for 1 hour
  2. distillationThe epichlorohydrin was distilled off under reduced pressure, water
  3. additionwas added
  4. extractionextracted with ethyl acetate
  5. dry with materialThe ethyl acetate phase was dried over anhydrous magnesium sulfate
  6. concentrationconcentrated
  7. custompurified by the silica gel chromatography
  8. customto obtain the intended product (Compound No. 33)
  9. customThe results of the elemental analysis

Sources & evidence

ORD record
ord-4a1e3e3dbe90403daa02509876296502
Source dataset
uspto-grants-1984_08
Patent number
US04468245

Reaction notes

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