3-Phenylprop-2-enoyl chloride → Monomethyl terephthalate 2-cinnamoylhydrazide

HRID 972178Notes

Reaction equation

HRID 972178 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:14]=[CH:13][C:8]([C:9]([NH:11][NH2:12])=[O:10])=[CH:7][CH:6]=1)=[O:4].[C:15](Cl)(=[O:24])[CH:16]=[CH:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>>[C:15]([NH:12][NH:11][C:9](=[O:10])[C:8]1[CH:13]=[CH:14][C:5]([C:3]([O:2][CH3:1])=[O:4])=[CH:6][CH:7]=1)(=[O:24])[CH:16]=[CH:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

3

Reactant 2

HCID 660233-Phenylprop-2-enoyl chlorideHCID 596004Methyl 4-(hydrazinecarbonyl)benzoate

Product 1

HCID 116185Monomethyl terephthalate 2-cinnamoylhydrazideYield 71.8%

Procedure

In a flask were placed 5 g of p-methoxycarbonylbenzoylhydrazine, 4.3 g of cinnamoyl chloride and 30 ml of N-dimethylacetamide, and the reaction was carried out with stirring at 30° - 40° C for 6 hours. After completion of the reaction, the produced precipitate was collected by filtration and washed with water. The so obtained precipitate was then recrystallized twice from acetic acid and dried under reduced pressure to yield 6 g of N-cinnamoyl-N'-(p-methoxycarbonylbenzoyl)hydrazine as white crystals, m.p. 207° C. Analysis: Calculated for C18H16N2O4 : C, 66.67%; H, 4.94%; N, 8.64%, Found: C, 66.51%; H, 4.98%; N, 8.71%.

Workup

  1. customIn a flask were placed
  2. customAfter completion of the reaction
  3. filtrationthe produced precipitate was collected by filtration
  4. washwashed with water
  5. customThe so obtained precipitate
  6. customwas then recrystallized twice from acetic acid
  7. customdried under reduced pressure

Sources & evidence

ORD record
ord-600b81f86be54bc88295e4cd08a292e4
Source dataset
uspto-grants-1977_10
Patent number
US04052362

Reaction notes

Loading…