Water → (N-Cyclopropyl-3-Trifluoromethylbenzylsulfonamido)Acetonitrile

HRID 1762301Notes

Reaction equation

HRID 1762301 reaction equation
[H-].[Na+].[CH:3]1([NH:6][S:7]([CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([C:17]([F:20])([F:19])[F:18])[CH:12]=2)(=[O:9])=[O:8])[CH2:5][CH2:4]1.Br[CH2:22][C:23]#[N:24].O>CN(C)C=O>[CH:3]1([N:6]([CH2:22][C:23]#[N:24])[S:7]([CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([C:17]([F:20])([F:18])[F:19])[CH:12]=2)(=[O:9])=[O:8])[CH2:5][CH2:4]1

Participants

6

Reactant 4

HCID 962Water3×HCID 11534BromoacetonitrileHCID 24758Sodium hydrideHCID 15615994N-cyclopropyl-3-trifluoromethylbenzylsulfonamide

Product 1

HCID 20043258(N-Cyclopropyl-3-Trifluoromethylbenzylsulfonamido)AcetonitrileYield 28.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

0.26 g of sodium hydride was added portion-wise to a solution containing 2.79 g of N-cyclopropyl-3-trifluoromethylbenzylsulfonamide in 50 ml of dimethylformamide over an ice bath. The mixture was stirred 15 minutes at 0l° C. and then 1.26 g of bromoacetonitrile was added drop-wise with cooling. The mixture was stirred overnight at room temperature. Water was then added resulting in the formation of a precipitate and oil. Addition of water was continued until no further precipitate or oil was formed. (About 150 ml of water was used.) The mix was cooled over an ice bath and then filtered. The filter cake was dissolved in hot cyclohexane and then recrystallized affording 0.9 g of the title compound as a solid m.p. 70.1°-71.0° C.

Workup

  1. temperaturewith cooling
  2. stirringThe mixture was stirred overnight at room temperature
  3. customresulting in the formation of a precipitate and oil
  4. customoil was formed
  5. filtrationfiltered
  6. dissolutionThe filter cake was dissolved in hot cyclohexane
  7. customrecrystallized

Sources & evidence

ORD record
ord-c58f835755bb4d32a86f2b847eca4a2c
Source dataset
uspto-grants-1989_05
Patent number
US04831179

Reaction notes

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