Phenylhydrazine → Benzoic acid, p-fluoro-, 2-phenylhydrazide

HRID 1197519Notes

Reaction equation

HRID 1197519 reaction equation
[C:1]1([NH:7][NH2:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.[F:16][C:17]1[CH:22]=[CH:21][C:20]([C:23](Cl)=[O:24])=[CH:19][CH:18]=1>CCOCC>[C:1]1([NH:7][NH:8][C:23](=[O:24])[C:20]2[CH:21]=[CH:22][C:17]([F:16])=[CH:18][CH:19]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 7516PhenylhydrazineHCID 8471TriethylamineHCID 678794-Fluorobenzoyl chloride

Product 1

HCID 15154Benzoic acid, p-fluoro-, 2-phenylhydrazideYield 60,111.801%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of phenylhydrazine (25 ml, 0.25 mmole) and triethylamine (35 ml, 0.25 mmole) in anhydrous ether (500 ml) was cooled down to -5° to -10° C. (ice-salt bath) under nitrogen and treated dropwise, over a 30 minute period, with 4-fluorobenzene carbonyl chloride (30 ml, 0.25 mole). The reaction mixture was warmed to room temperature, stirred for 3.0 hours, then filtered, washing the solids well with ether (200 ml). The solids were dissolved in dichloromethane (600 ml), stripped to near dryness, suspended in hexane (600 ml) and filtered. The clear filtrate was evaporated to dryness, triturated with tetrahydrofuran (700 ml) and filtered, washing the solids well with tetrahydrofuran (100 ml). The filtrate was evaporated to dryness and dried in vacuo to give a crude product (34.6 g) contaminated with two other components.

Workup

  1. filtrationfiltered
  2. washwashing the solids well with ether (200 ml)
  3. dissolutionThe solids were dissolved in dichloromethane (600 ml)
  4. filtrationfiltered
  5. customThe clear filtrate was evaporated to dryness
  6. customtriturated with tetrahydrofuran (700 ml)
  7. filtrationfiltered
  8. washwashing the solids well with tetrahydrofuran (100 ml)
  9. customThe filtrate was evaporated to dryness
  10. customdried in vacuo

Sources & evidence

ORD record
ord-7502877eb47b4af7b411fac79b1f13e8
Source dataset
uspto-grants-1994_01
Patent number
US05276021

Reaction notes

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