Formaldehyde → HCID 19786514, compound

HRID 1031243Notes

Reaction equation

HRID 1031243 reaction equation
[F:1][C:2]([F:31])([F:30])[C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10]([N:12]2[CH2:16][CH:15]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH:14]([C:23]3[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][CH:24]=3)[NH:13]2)=[O:11])=[CH:5][CH:4]=1.[CH2:32]=O>C(O)=O>[O:11]=[C:10]1[N:12]2[CH2:16][CH:15]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH:14]([C:23]3[CH:24]=[CH:25][C:26]([Cl:29])=[CH:27][CH:28]=3)[N:13]2[CH2:32][N:9]1[C:6]1[CH:7]=[CH:8][C:3]([C:2]([F:1])([F:30])[F:31])=[CH:4][CH:5]=1

Participants

4

Reactant 2

HCID 712FormaldehydeHCID 19786515HCID 19786515, compound

Product 1

HCID 19786514HCID 19786514, compound

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

To 1.0 g (2.2 mmole) of N-(4-trifluoromethylphenyl)-3-(4-chlorophenyl)-4-phenyl-2,3,4,5-tetrahydro-1H-pyrazole-1-carboxamide in 5 ml of formic acid was added 0.57 g of formalin. The mixture was heated at reflux for 30 minutes and then partitioned between dichloromethane and water. The organic layer was washed with water and brine and then dried over anhydrous magnesium sulfate. Filtration, concentration in vacuo, and chromatography on silica gel using diethyl ether and hexanes gave the expected compound, mp 184°-187° C.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 30 minutes
  3. custompartitioned between dichloromethane and water
  4. washThe organic layer was washed with water and brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationFiltration, concentration in vacuo, and chromatography on silica gel

Sources & evidence

ORD record
ord-46cb1a9f1b87462b8a1d1d2a420aae72
Source dataset
uspto-grants-1992_04
Patent number
US05109014

Reaction notes

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