Chloral → Benzoic acid, 2-(2,2,2-trichloroethylidene)hydrazide

HRID 261507Notes

Reaction equation

HRID 261507 reaction equation
[C:1]([NH:9][NH2:10])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O=[CH:12][C:13]([Cl:16])([Cl:15])[Cl:14]>C1C=CC=CC=1>[C:1]([NH:9][N:10]=[CH:12][C:13]([Cl:16])([Cl:15])[Cl:14])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6407ChloralHCID 11955Benzoylhydrazine

Product 1

HCID 53650662Benzoic acid, 2-(2,2,2-trichloroethylidene)hydrazide

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

10 g (0.073 mol) of benzoylhydrazine were suspended in benzene, 200 ml, and 18.3 g (0.124 mol) of chloral were added dropwise to the suspension which was then refluxed under agitation for 3 hours. Upon cooling, the sedimented crystals were collected by filtration and washed well with benzene. In this way, white brown crystals, 19 g, were obtained substantially quantatively. m.p. 188°-189° C. (decomposed). When recrystallized from acetone, the Compound No. 1, m.p. 194°-195° (decomposed), was obtained in white needles. Yield: 15.4 g (81% of the theoretical).

Workup

  1. temperaturewas then refluxed under agitation for 3 hours
  2. temperatureUpon cooling
  3. filtrationthe sedimented crystals were collected by filtration
  4. washwashed well with benzene
  5. customIn this way, white brown crystals, 19 g, were obtained substantially quantatively
  6. customWhen recrystallized from acetone
  7. custom1, m.p. 194°-195° (decomposed), was obtained in white needles

Sources & evidence

ORD record
ord-b39336166e5b4ab5b399ac435939e4a4
Source dataset
uspto-grants-1979_08
Patent number
US04166129

Reaction notes

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