Triethylamine → HCID 12813186, compound

HRID 1154984Notes

Reaction equation

HRID 1154984 reaction equation
C[N:2]1[CH:6]=[C:5]([C:7]2[CH:8]=[C:9]([C:13]([F:16])([F:15])[F:14])[CH:10]=[CH:11][CH:12]=2)[C:4](=[O:17])[N:3]1[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.Cl.[F:25]C1C=CC(NN)=CC=1.C(N(CC)CC)C>C1C=CC=CC=1>[F:25][C:21]1[CH:22]=[CH:23][C:18]([N:3]2[C:4](=[O:17])[C:5]([C:7]3[CH:8]=[C:9]([C:13]([F:16])([F:15])[F:14])[CH:10]=[CH:11][CH:12]=3)=[CH:6][NH:2]2)=[CH:19][CH:20]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 699814-Fluorophenylhydrazine hydrochlorideHCID 128131761,2-Dihydro-1-methyl-2-phenyl-4-[3-(trifluoromethyl)phenyl]-3H-pyrazol-3-one

Product 1

HCID 12813186HCID 12813186, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

A 5.5 gram portion of the atropic ester of Example 1 was combined with 3.5 grams of 4-fluorophenylhydrazine hydrochloride and 2 grams triethylamine in 50 ml. benzene. The mixture was stirred at reflux temperature for 5 hours, after which about half of the benzene was allowed to evaporate and an equivalent amount of meta-xylene was added. The mixture was then stirred at reflux overnight, and the reaction mixture was evaporated to dryness under vacuum. The residue was partitioned between ethyl acetate and water, and the organic layer was dried over sodium sulfate and evaporated to dryness. The residue was chromatographed on silica gel with ethyl acetate as the eluant. The product containing fractions were combined and evaporated to dryness to produce about 3.5 grams of crude intermediate, which was recrystallized from methanol to produce 2.7 grams of purified 1-(4-fluorophenyl)-4-(α,α,α-trifluoro-3-tolyl)-3-pyrazolin-5-one, m.p. 171°-173° C.

Workup

  1. temperatureat reflux temperature for 5 hours
  2. customto evaporate
  3. additionan equivalent amount of meta-xylene was added
  4. stirringThe mixture was then stirred
  5. temperatureat reflux overnight
  6. customthe reaction mixture was evaporated to dryness under vacuum
  7. customThe residue was partitioned between ethyl acetate and water
  8. dry with materialthe organic layer was dried over sodium sulfate
  9. customevaporated to dryness
  10. customThe residue was chromatographed on silica gel with ethyl acetate as the eluant
  11. additionThe product containing fractions
  12. customevaporated to dryness
  13. customto produce about 3.5 grams of crude intermediate, which
  14. customwas recrystallized from methanol

Sources & evidence

ORD record
ord-caf41d2100e54e659454403495bd84b8
Source dataset
uspto-grants-1981_11
Patent number
US04299614

Reaction notes

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