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

HRID 2226447Notes

Reaction equation

HRID 2226447 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 pH 4 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-b0206b91115a4a1d85fd9cae1f1c6900
Source dataset
uspto-grants-1994_09
Patent number
US05348967

Reaction notes

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