Benzoyl chloride → HCID 15294600, compound

HRID 21620Notes

Reaction equation

HRID 21620 reaction equation
[CH2:1]([NH:6][NH:7][C:8](=[O:15])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:2]([CH3:5])([CH3:4])[CH3:3].[C:16](Cl)(=[O:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[OH-].[Na+]>C1(C)C=CC=CC=1.CCCCCC>[CH2:1]([N:6]([C:16](=[O:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[NH:7][C:8](=[O:15])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:2]([CH3:5])([CH3:4])[CH3:3]

Participants

6

Reactant 3

HCID 7412Benzoyl chlorideHCID 14798Sodium HydroxideHCID 19367924HCID 19367924, compound

Product 1

HCID 15294600HCID 15294600, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolvent2×HCID 8058HexaneSolvent

Procedure

To a stirred solution of the 2-neopentyl-1-benzoylhydrazine in toluene (40 ml) at 5° C. were added dropwise and simultaneously solutions of benzoyl chloride (1.4 g, 10 mmoles) in toluene (5 ml) and aqueous 50% sodium hydroxide solution (0.8 g) while maintaining the temperature below 10° C. After the addition, the reaction mixture was warmed to room temperature and stirred for 1 hour. The reaction mixture was diluted with hexane and the precipitated product isolated by filtration. The product was washed with water and hexane and dried. The crude product was recrystallized from methanol to afford N'-neopentyl-N,N'-dibenzoylhydrazine as a white powder: m.p. 237°-239° C.

Workup

  1. additionAfter the addition
  2. customthe precipitated product isolated by filtration
  3. washThe product was washed with water and hexane
  4. customdried
  5. customThe crude product was recrystallized from methanol

Sources & evidence

ORD record
ord-6d8af3c84f26461188610444f65703d4
Source dataset
uspto-grants-1995_06
Patent number
US05424333

Reaction notes

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