Ethylamine → N-ethyl-5-(1-methyl-3-trifluoromethyl-1H-pyrazol-5-yl)thiophene-2-carboxamide

HRID 1699764Notes

Reaction equation

HRID 1699764 reaction equation
[CH3:1][N:2]1[C:6]([C:7]2[S:11][C:10]([C:12](Cl)=[O:13])=[CH:9][CH:8]=2)=[CH:5][C:4]([C:15]([F:18])([F:17])[F:16])=[N:3]1.C1COCC1.[CH2:24]([NH2:26])[CH3:25]>O>[CH2:24]([NH:26][C:12]([C:10]1[S:11][C:7]([C:6]2[N:2]([CH3:1])[N:3]=[C:4]([C:15]([F:18])([F:17])[F:16])[CH:5]=2)=[CH:8][CH:9]=1)=[O:13])[CH3:25]

Participants

5

Reactant 3

HCID 6341EthylamineHCID 8028Tetrahydrofuran2×HCID 120202255-(1-methyl-3-trifluoromethyl-1H-pyrazol-5-yl)thiophene-2-carbonyl chloride

Product 1

HCID 22288409N-ethyl-5-(1-methyl-3-trifluoromethyl-1H-pyrazol-5-yl)thiophene-2-carboxamide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

5-(1-Methyl-3-trifluoromethyl-1H-pyrazol-5-yl)thiophene-2-carbonyl chloride (150 mg) and THF (2 ml) were added to a mixture of 70% ethylamine aqueous solution (1 ml) and THF (2 ml), followed by stirring at room temperature for 2 hours. Water was added to the reaction solution, the thus formed product was extracted with ethyl acetate and then the extract was washed with saturated brine. The organic layer was dried over anhydrous magnesium sulfate and then concentrated under a reduced pressure. The resulting residue was recrystallized from a mixed solvent ethyl acetate and n-hexane to give N-ethyl-5-(1-methyl-3-trifluoromethy-1H-pyrazol-5-yl)thiophene-2-carboxamide (96 mg) as colorless powder crystals.

Workup

  1. extractionthe thus formed product was extracted with ethyl acetate
  2. washthe extract was washed with saturated brine
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. concentrationconcentrated under a reduced pressure
  5. customThe resulting residue was recrystallized from a mixed solvent ethyl acetate and n-hexane

Sources & evidence

ORD record
ord-5eec5e891d7e4020892d2596f2027737
Source dataset
uspto-grants-2002_02
Patent number
US06348480B1

Reaction notes

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