Potassium Carbonate → (N-Methyl-3-Trifluoromethylbenzylsulfonamido)Acetonitrile

HRID 1762298Notes

Reaction equation

HRID 1762298 reaction equation
[F:1][C:2]([F:15])([F:14])[C:3]1[CH:4]=[C:5]([CH:11]=[CH:12][CH:13]=1)[CH2:6][S:7](Cl)(=[O:9])=[O:8].[CH3:16][NH:17][CH2:18][C:19]#[N:20].C(=O)([O-])[O-].[K+].[K+]>O>[CH3:16][N:17]([CH2:18][C:19]#[N:20])[S:7]([CH2:6][C:5]1[CH:11]=[CH:12][CH:13]=[C:3]([C:2]([F:15])([F:14])[F:1])[CH:4]=1)(=[O:9])=[O:8]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 36652Acetonitrile, 2-(methylamino)-HCID 27946463-(Trifluoromethyl)phenylmethanesulfonyl chloride

Product 1

HCID 15615993(N-Methyl-3-Trifluoromethylbenzylsulfonamido)Acetonitrile

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

In this example 36.1 g of 3-trifluoromethylbenzylsulfonyl chloride was added cautiously to a solution containing 29.8 g of the hydrochloride salt of methylaminoacetonitrile and 38.7 g of potassium carbonate in 130 ml of water at room temperature. The reaction mixture was maintained at about 70° C. for about four hours. The mixture was allowed to cool and then extracted with ethyl ether. The ethyl ether extract was dried over magnesium sulfate and evaporated to dryness. The residue was vacuum filtered through silica gel using 3% vol. tetrahydrofuran: chloroform as eluent. 29 g of the title compound was obtained as a waxy white solid.

Workup

  1. temperatureto cool
  2. extractionextracted with ethyl ether
  3. extractionThe ethyl ether extract
  4. dry with materialwas dried over magnesium sulfate
  5. customevaporated to dryness
  6. filtrationfiltered through silica gel using 3% vol. tetrahydrofuran

Sources & evidence

ORD record
ord-75d1dcd69b9e4abab9a3ac4316916b70
Source dataset
uspto-grants-1989_05
Patent number
US04831179

Reaction notes

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