Methanol → HCID 53814536, compound

HRID 328527Notes

Reaction equation

HRID 328527 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[Cl:12])[C:5]([O:7]C)=O.[C:13]1([NH:19][NH2:20])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C[O-].[Na+].CO>O>[C:13]1([N:19]([C:5](=[O:7])[C:4]2[CH:9]=[CH:10][C:11]([Cl:12])=[C:2]([Cl:1])[CH:3]=2)[NH2:20])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 7516PhenylhydrazineHCID 76193Benzoic acid, 3,4-dichloro-, methyl esterHCID 10942334Sodium Methoxide

Product 1

HCID 53814536HCID 53814536, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
25 °C

Procedure

A mixture consisting of 71.8 g. (0.35 mole) methyl 3,4-dichlorobenzoate, 37.9 g. (0.35 mole) phenylhydrazine, 21.6 g. (0.40 mole) sodium methoxide, and 175 ml. methanol was heated at the reflux temperature for 22 hrs. After cooling the reaction mixture to about 25° C., it was poured into 500 ml. water. The aqueous mixture was filtered and the solids that collected on the filter were dissolved in 500 ml. ethanol. Refrigeration caused crystals to form which were recovered by filtration. There was thus obtained 3,4-dichlorobenzoic acid phenylhydrazide melting at 169° to 172° C. An analytical sample melting at 171.5° to 173° C. was obtained by recrystallization from ethanol.

Workup

  1. additionit was poured into 500 ml
  2. filtrationThe aqueous mixture was filtered
  3. customthe solids that collected on the filter
  4. dissolutionwere dissolved in 500 ml
  5. customto form which
  6. filtrationwere recovered by filtration
  7. customAn analytical sample melting at 171.5° to 173° C. was obtained by recrystallization from ethanol

Sources & evidence

ORD record
ord-1cea3d011ecc4d1fa776f78ddd23326c
Source dataset
uspto-grants-1977_04
Patent number
US04017540

Reaction notes

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