Acetonitrile → HCID 15766693, compound

HRID 1196782Notes

Reaction equation

HRID 1196782 reaction equation
Cl[C:2]([O:4][CH3:5])=[O:3].C(#N)C.[F:9][C:10]([F:22])([F:21])[C:11]1[C:12]([S:17]([NH2:20])(=[O:19])=[O:18])=[N:13][CH:14]=[CH:15][CH:16]=1>C(N(CC)CC)C>[F:21][C:10]([F:9])([F:22])[C:11]1[C:12]([S:17]([NH:20][C:2](=[O:3])[O:4][CH3:5])(=[O:19])=[O:18])=[N:13][CH:14]=[CH:15][CH:16]=1

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 6586Methyl chloroformateHCID 139109213-(Trifluoromethyl)pyridine-2-sulfonamide

Product 1

HCID 15766693HCID 15766693, compoundYield 44.2%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

Methyl chloroformate (3.31 g, 35 mmol) was added under cooling with ice to a dry acetonitrile (150 ml) solution containing 3-trifluoromethylpyridine-2-sulfonamide (7.91 g, 35 mmol) and triethylamine (16 ml), and the mixture was continuously stirred at room temperature for 3 hours. Then, the solvent was distilled off under reduced pressure, and the residue was dissolved in 300 ml of water. A small amount of insoluble substances were removed by filtration, and the filtrate was adjusted to pH of 1 to 2 with concentrated hydrochloric acid under cooling with ice. Precipitated crystals were collected by filtration and thoroughly washed with water, then washed with a solvent mixture of ethyl ether/n-hexane and dried to obtain 4.4 g of desired methyl N-(3-trifluoromethylpyridine-2-sulfonyl)carbamate. Melting point: 128°-129° C.

Workup

  1. distillationThen, the solvent was distilled off under reduced pressure
  2. dissolutionthe residue was dissolved in 300 ml of water
  3. customA small amount of insoluble substances were removed by filtration
  4. temperatureunder cooling with ice
  5. customPrecipitated crystals
  6. filtrationwere collected by filtration
  7. washthoroughly washed with water
  8. washwashed with a solvent mixture of ethyl ether/n-hexane
  9. customdried

Sources & evidence

ORD record
ord-41bcac865a454fb98188abc3140aafcb
Source dataset
uspto-grants-1992_05
Patent number
US05116405

Reaction notes

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