Diethyl Ether → Benzoic acid, p-fluoro-, 2-phenylhydrazide

HRID 65268Notes

Reaction equation

HRID 65268 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](Cl)=[O:7])=[CH:4][CH:3]=1.[C:11]1([NH:17][NH2:18])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C(N(CC)CC)C.C(OCC)C>O1CCCC1>[C:11]1([NH:17][NH:18][C:6](=[O:7])[C:5]2[CH:9]=[CH:10][C:2]([F:1])=[CH:3][CH:4]=2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 7516PhenylhydrazineHCID 8471TriethylamineHCID 678794-Fluorobenzoyl chloride

Product 1

HCID 15154Benzoic acid, p-fluoro-, 2-phenylhydrazide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

30 ml. (0.25 mole) of 4-fluorobenzoyl chloride is added dropwise over a 30 minute period to a mixture of 25 ml. (0.25 mole) of phenylhydrazine and 35 ml. (0.25 mole) of triethylamine in 500 ml. of anhydrous diethyl ether stirred at -10° C. under nitrogen. The reaction mixture is allowed to warm to 20°-25° C. and stirred under nitrogen for 3 hours. The obtained solids are collected by filtration, washed with diethyl ether and dissolved in about 600 ml. of methylene chloride. The methylene chloride solution is filtered and evaporated at reduced pressure to near dryness, and n-hexane is added to obtain the crude solid product (26 g.). The crude product is dissolved in tetrahydrofuran and filtered to remove the triethylamine hydrochloride, the tetrahydrofuran is evaporated at reduced pressure, and the obtained product is recrystallized from acetone (12 g.), m.p. 181°-186° C. A second crop is also obtained (6 g.).

Workup

  1. temperatureto warm to 20°-25° C.
  2. filtrationThe obtained solids are collected by filtration
  3. washwashed with diethyl ether
  4. dissolutiondissolved in about 600 ml
  5. filtrationThe methylene chloride solution is filtered
  6. customevaporated at reduced pressure
  7. additionis added
  8. customto obtain the crude solid product (26 g.)
  9. filtrationfiltered
  10. customto remove the triethylamine hydrochloride
  11. customthe tetrahydrofuran is evaporated at reduced pressure
  12. customthe obtained product is recrystallized from acetone (12 g.), m.p. 181°-186° C
  13. customA second crop is also obtained (6 g.)

Sources & evidence

ORD record
ord-d4670f54af29436bb92c082e4821b644
Source dataset
uspto-grants-1986_09
Patent number
US04613610

Reaction notes

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