Nitric Acid → N-(3-nitro-5-trifluoromethyl-2-pyridyl)ethanesulfonamide

HRID 257028Notes

Reaction equation

HRID 257028 reaction equation
[F:1][C:2]([F:16])([F:15])[C:3]1[CH:4]=[CH:5][C:6]([NH:9][S:10]([CH2:13][CH3:14])(=[O:12])=[O:11])=[N:7][CH:8]=1.[N+:17]([O-])([OH:19])=[O:18]>C(O)(=O)C>[N+:17]([C:5]1[C:6]([NH:9][S:10]([CH2:13][CH3:14])(=[O:12])=[O:11])=[N:7][CH:8]=[C:3]([C:2]([F:1])([F:15])[F:16])[CH:4]=1)([O-:19])=[O:18]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 10610926N-(5-trifluoromethyl-2-pyridyl)ethanesulfonamide

Product 1

HCID 10851681N-(3-nitro-5-trifluoromethyl-2-pyridyl)ethanesulfonamideYield 90.2%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
80 °C

Procedure

45 g of N-(5-trifluoromethyl-2-pyridyl)ethanesulfonamide was dissolved in 112.5 ml of acetic acid. While heating it to a temperature of from 100° to 105° C., 26 g of fuming nitric acid (94%) was dropwise added, and the mixture was reacted for further 6 hours. The reaction product was left to cool to 80° C., and then poured into 2 l of ice water. Precipitated crystals were collected by filtration, washed with water and dried to obtain 47.8 g of N-(3-nitro-5-trifluoromethyl-2-pyridyl)ethanesulfonamide.

Workup

  1. additionwas dropwise added
  2. customthe mixture was reacted for further 6 hours
  3. waitThe reaction product was left
  4. customPrecipitated crystals
  5. filtrationwere collected by filtration
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-2e1a3315d6034171a923f2c64a0975f3
Source dataset
uspto-grants-1993_11
Patent number
US05260320

Reaction notes

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