Water → Rufinamide

HRID 651250Notes

Reaction equation

HRID 651250 reaction equation
[F:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]([F:12])[C:3]=1[CH2:4][N:5]=[N+:6]=[N-:7].[OH2:13]>>[F:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]([F:12])[C:3]=1[CH2:4][N:5]1[CH:2]=[C:3]([C:4]([NH2:5])=[O:13])[N:7]=[N:6]1

Participants

3

Reactant 2

HCID 962WaterHCID 108883232-(Azidomethyl)-1,3-difluorobenzene

Product 1

HCID 129228Rufinamide

Conditions

Temperature
82 °C

Procedure

A mixture of 2,6-difluorobenzylazide (9,22 g), 2-chloroacryonitrile (6,68 g) and water is stirred at about 82° C. for about 24 hours. 2-Chloroacrylnitrile is distilled off by raising the external temperature to about 113° C. excess. The mixture is cooled to about 40° C. and toluene (10 ml) is added. Within about 40 minutes at about 80° C. sodium hydroxide (5,5 ml—30%) is added the amide being crystallized. By raising the external temperature to 112° C., toluene is distilled off. The suspension is cooled to 20° C. and the product is isolated by filtration, washed with water (200 ml) and dried at about 60° C. in vacuo.

Workup

  1. distillation2-Chloroacrylnitrile is distilled off
  2. temperatureby raising the external temperature to about 113° C. excess
  3. temperatureThe mixture is cooled to about 40° C.
  4. additiontoluene (10 ml) is added
  5. additionWithin about 40 minutes at about 80° C. sodium hydroxide (5,5 ml—30%) is added the amide being
  6. customcrystallized
  7. temperatureBy raising the external temperature to 112° C.
  8. distillationtoluene is distilled off
  9. temperatureThe suspension is cooled to 20° C.
  10. customthe product is isolated by filtration
  11. washwashed with water (200 ml)
  12. customdried at about 60° C. in vacuo

Sources & evidence

ORD record
ord-4da494bc4a984578a5d484d0467c5ca0
Source dataset
uspto-grants-2001_08
Patent number
US06277999B1

Reaction notes

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