Methanol → Ethyl 1,3,5-triphenyl-4,5-dihydropyrazole-4-carboxylate

HRID 2235579Notes

Reaction equation

HRID 2235579 reaction equation
[C:1]([O:11][CH2:12][CH3:13])(=[O:10])[CH:2]=[CH:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[C:14]1([NH:20][N:21]=[CH:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.CC1C=CC(S([N-]Cl)(=O)=O)=CC=1.O.O.O.[Na+].CO>C(OCC)(=O)C>[C:14]1([N:20]2[CH:3]([C:4]3[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=3)[CH:2]([C:1]([O:11][CH2:12][CH3:13])=[O:10])[C:22]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[N:21]2)[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 7649Ethyl 3-phenylprop-2-enoateHCID 95800DiphenylhydrazoneHCID 517414chloramine-T trihydrate

Product 1

HCID 13843974Ethyl 1,3,5-triphenyl-4,5-dihydropyrazole-4-carboxylate

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of ethyl cinnamate (7, 2.55 g), benzaldehyde phenylhydrazone (2, 4.21 g), chloramine-T trihydrate (6.45 g), and methanol (45 mL) were heated under refluxing for 22 hours. The reaction mixture was diluted with 50% ethyl acetate in n-hexanes (400 mL), filtered, and evaporated. The residue was purified by column chromatography (silica gel 200 g, eluent: 0 to 10% ethyl acetate gradient in hexanes) and evaporated to give FN1-1 (8, 1.25 g) as colorless crystal. 1H NMR (CDCl3, 400 MHz) δ 7.66-7.64 (m, 1H), 7.46-7.22 (m, 13H), 6.88 (t, J=7.2 Hz, 1H), 4.81 (d, J=4.0 Hz, 1H), 4.70 (d, J=4.0 Hz, 1H), 4.07 (quartet, J=7.2 Hz, 2H), 0.97 (t, J=7.2 Hz, 3H). MS: 371.9 (M+H), 325.5, 297.5.

Workup

  1. temperaturewere heated
  2. temperatureunder refluxing for 22 hours
  3. filtrationfiltered
  4. customevaporated
  5. customThe residue was purified by column chromatography (silica gel 200 g, eluent: 0 to 10% ethyl acetate gradient in hexanes)
  6. customevaporated
  7. customto give FN1-1 (8, 1.25 g) as colorless crystal

Sources & evidence

ORD record
ord-0ece9c83bcef461b85af1ff412b7df3c
Source dataset
uspto-grants-2010_05
Patent number
US07714014B2

Reaction notes

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