Phenylacetic Acid → HCID 86734394, compound

HRID 1414841Notes

Reaction equation

HRID 1414841 reaction equation
[C:1]([NH:11][NH2:12])(=[O:10])[CH2:2][CH2:3][CH2:4][CH2:5][C:6]([NH:8][NH2:9])=[O:7].[C:13]1(CC(O)=O)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.N1[CH:28]=[CH:27]C=CC=1.S(Cl)(Cl)=[O:30].Cl[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1>>[C:34]1([N:8]([C:6](=[O:7])[CH:5]([C:27](=[O:30])[CH3:28])[CH2:4][CH2:3][CH2:2][C:1]([NH:11][NH2:12])=[O:10])[NH:9][C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1

Participants

6

Reactant 5

HCID 999Phenylacetic AcidHCID 1049PyridineHCID 7964ChlorobenzeneHCID 24386Thionyl ChlorideHCID 66117Adipic Dihydrazide

Product 1

HCID 86734394HCID 86734394, compoundYield 63%

Procedure

17.4 g (0.1 mol) of adipic acid dihydrazide and 27.2 g (0.2 mol) of phenylacetic acid are suspended in 230 ml of chlorobenzene, 2.0 g (0.025 mol) of pyridine are added and the mixture is heated to the boil. Thereafter 26.2 g (0.22 mol) of thionyl chloride are added dropwise, whereupon the vigorous reaction commences. The suspension turns slightly brown. After boiling for 1 hour it is cooled and filtered and the product is washed with methanol. N,N'-Diphenylacetyl-adipic acid dihydrazide of melting point 310°-312° C is thus obtained in 63% yield.

Workup

  1. temperaturethe mixture is heated to the boil
  2. temperatureit is cooled
  3. filtrationfiltered
  4. washthe product is washed with methanol

Sources & evidence

ORD record
ord-8a804a9ae53d4d2e931ce7ad70bd2aec
Source dataset
uspto-grants-1977_01
Patent number
US04002680

Reaction notes

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