Ammonia → Rufinamide

HRID 541036Notes

Reaction equation

HRID 541036 reaction equation
[F:1][C:2]1[CH:16]=[CH:15][CH:14]=[C:13]([F:17])[C:3]=1[CH2:4][N:5]1[CH:9]=[C:8]([C:10](O)=[O:11])[N:7]=[N:6]1.S(Cl)(Cl)=O.[NH3:22]>>[CH:15]1[CH:14]=[C:13]([F:17])[C:3]([CH2:4][N:5]2[N:6]=[N:7][C:8]([C:10]([NH2:22])=[O:11])=[CH:9]2)=[C:2]([F:1])[CH:16]=1

Participants

4

Reactant 3

HCID 222AmmoniaHCID 24386Thionyl ChlorideHCID 10014469Cgp-47292

Product 1

HCID 129228Rufinamide

Conditions

Temperature
80 °C

Procedure

A mixture of 1-(2,6-difluorobenzyl)-1H-1,2,3-triazole-4-carboxylic acid (25 gms) and thionyl chloride (63.5 gms) were stirred at 80° C. and maintained for 3 hours. The reaction mass was cooled to 50° C. and excess thionyl chloride was distilled off. To this reaction mass toluene (25 ml) was charged twice and it was distilled off under vacuum it was followed by addition of toulene (175 ml) to get clear solution. Aqueous ammonia (100 ml) charged into reaction mass at room temperature and maintained for 2 hours. The reaction mass was filtered. 10% sodium carbonate solution was added to above solid and stirred for 30 minutes. The solid was filtered and washed with water and cyclohexane (50 ml). Dried the crude material in a vacuum oven at 70-80° C. for 10 hours. Yield: 23.00 gm.

Workup

  1. temperaturemaintained for 3 hours
  2. temperatureThe reaction mass was cooled to 50° C.
  3. distillationexcess thionyl chloride was distilled off
  4. additionTo this reaction mass toluene (25 ml) was charged twice
  5. distillationit was distilled off under vacuum it
  6. additionwas followed by addition of toulene (175 ml)
  7. customto get clear solution
  8. temperaturemaintained for 2 hours
  9. filtrationThe reaction mass was filtered
  10. addition10% sodium carbonate solution was added to above solid
  11. stirringstirred for 30 minutes
  12. filtrationThe solid was filtered
  13. washwashed with water and cyclohexane (50 ml)
  14. dry with materialDried the crude material in a vacuum oven at 70-80° C. for 10 hours

Sources & evidence

ORD record
ord-4265b18b507e4fb8aae24dcb0eb4fdad
Source dataset
uspto-grants-2014_10
Patent number
US08871945B2

Reaction notes

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