Water → N-(5-trifluoromethyl-2-pyridyl)ethanesulfonamide

HRID 484091Notes

Reaction equation

HRID 484091 reaction equation
[CH2:1]([S:3]([NH2:6])(=[O:5])=[O:4])[CH3:2].Cl[C:8]1[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:16])[F:15])=[CH:10][N:9]=1.C(=O)([O-])[O-].[K+].[K+].O>CS(C)=O>[F:15][C:14]([F:17])([F:16])[C:11]1[CH:12]=[CH:13][C:8]([NH:6][S:3]([CH2:1][CH3:2])(=[O:5])=[O:4])=[N:9][CH:10]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 73702EthanesulfonamideHCID 923422-Chloro-5-(trifluoromethyl)pyridine

Product 1

HCID 10610926N-(5-trifluoromethyl-2-pyridyl)ethanesulfonamideYield 72%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
130 °C

Procedure

20.3 g of ethanesulfonamide and 26.0 g of 2-chloro-5-trifluoromethylpyridine were dissolved in 220 ml of dimethylsulfoxide, and 47.4 g of anhydrous potassium carbonate was further added thereto. This solution mixture was heated to 130° C. and reacted for 5 hours. After completion of the reaction, the reaction product was poured into 1 l of water. Undissolved materials in water were extracted with ethyl ether and removed. Then, the aqueous layer was adjusted to pH4 with concentrated hydrochloric acid, and precipitated crystals were collected by filtration and dried to obtain 26.2 g of N-(5-trifluoromethyl-2-pyridyl)ethanesulfonamide having a melting point of from 164° to 165° C.

Workup

  1. customreacted for 5 hours
  2. customAfter completion of the reaction
  3. extractionUndissolved materials in water were extracted with ethyl ether
  4. customremoved
  5. customprecipitated crystals
  6. filtrationwere collected by filtration
  7. customdried

Sources & evidence

ORD record
ord-63b3218f5db842278bd6a35d50b0a90c
Source dataset
uspto-grants-1993_07
Patent number
US05229403

Reaction notes

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