Triethylamine → HCID 12813178, compound

HRID 1154979Notes

Reaction equation

HRID 1154979 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.[Cl:25]C1C=C(NN)C=CC=1.C(N(CC)CC)C>C1(C)C=CC=C(C)C=1>[Cl:25][C:20]1[CH:19]=[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:23]=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 75331m-Chlorophenylhydrazine hydrochlorideHCID 128131761,2-Dihydro-1-methyl-2-phenyl-4-[3-(trifluoromethyl)phenyl]-3H-pyrazol-3-one

Product 1

HCID 12813178HCID 12813178, compound

Reagents, catalysts & solvents 1

HCID 7929M-XyleneSolvent

Procedure

A 3.5 gram portion of the atropic ester of Example 1 was reacted with 2.3 grams 3-chlorophenylhydrazine hydrochloride in the presence of 1.3 grams triethylamine in about 50 ml. meta-xylene. The mixture was then stirred at reflux overnight, and the reaction mixture 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 a crude product, which was recrystallized from methanol to produce 2 grams 1-(3-chlorophenyl)-4-(α,α,α-trifluoro-3-tolyl)-3-pyrazolin-5-one, m.p. 182°-184° C.

Workup

  1. temperatureat reflux overnight
  2. customthe reaction mixture evaporated to dryness under vacuum
  3. customThe residue was partitioned between ethyl acetate and water
  4. dry with materialthe organic layer was dried over sodium sulfate
  5. customevaporated to dryness
  6. customThe residue was chromatographed on silica gel with ethyl acetate as the eluant
  7. additionThe product containing fractions
  8. customevaporated to dryness
  9. customto produce a crude product, which
  10. customwas recrystallized from methanol

Sources & evidence

ORD record
ord-209559267bdf4e16842776d17528a7d2
Source dataset
uspto-grants-1981_11
Patent number
US04299614

Reaction notes

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