Methanol → HCID 21548697, compound

HRID 1580472Notes

Reaction equation

HRID 1580472 reaction equation
[F:1][C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8]CC)=O)=[CH:4][CH:3]=1.CO.[C:15]1([NH:21][NH2:22])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C[O-].[Na+]>O>[C:15]1([N:21]([C:6](=[O:8])[C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:12][CH:11]=2)[NH2:22])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 7516PhenylhydrazineHCID 67976Benzoic acid, 4-fluoro-, ethyl esterHCID 10942334Sodium Methoxide

Product 1

HCID 21548697HCID 21548697, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
25 °C

Procedure

A mixture consisting of 101.2 g. (0.602 mole) ethyl p-fluorobenzoate, 250 ml. methanol, 70.0 g. (0.646 mole) phenylhydrazine, and 33.6 g. (0.621 mole) sodium methoxide (mixed in that order) was heated at the reflux temperature for 16 hrs. After cooling the reaction mixture to about 25°C it was poured into 1500 ml. water. The aqueous mixture was filtered, and the filter cake was washed with water and recrystallized from 95% aqueous ethanol. The crystals melted at 174° to 178°C. An analytical sample of p-fluorobenzoic acid phenylhydrazide melting at 177° to 179°C. was obtained by recrystallizing once from a mixture of ethyl acetate and Skellysolve B (essentially a mixture of isomeric hexanes boiling in the range of 146° to 156°F.), and once from 75% aqueous ethanol.

Workup

  1. temperaturewas heated at the reflux temperature for 16 hrs
  2. additionwas poured into 1500 ml
  3. filtrationThe aqueous mixture was filtered
  4. washthe filter cake was washed with water
  5. customrecrystallized from 95% aqueous ethanol

Sources & evidence

ORD record
ord-51df70cc5fd54e7c8169422ebb4ae189
Source dataset
uspto-grants-1976_01
Patent number
US03932661

Reaction notes

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