Water → 4-Chloro-N'-(diphenylmethylene)butanehydrazide

HRID 8204

Reaction equation

HRID 8204 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][C:5](Cl)=[O:6].[C:8](=[N:21][NH2:22])([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.N1C=CC=CC=1.O>ClCCl>[C:8](=[N:21][NH:22][C:5](=[O:6])[CH2:4][CH2:3][CH2:2][Cl:1])([C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 783704-Chlorobutyryl chlorideHCID 79304Diphenylmethylidenehydrazine

Product 1

HCID 3198334-Chloro-N'-(diphenylmethylene)butanehydrazide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-Chlorobutyryl chloride (57 mL, 510 mmol) is added to a solution of benzophenone hydrazone (100 g, 510 mmol) and pyridine (41 mL, 510 mmol) in anhydrous dichloromethane (520 mL) under nitrogen at a rate that maintains a gentle reflux throughout the addition. The mixture is stirred for 0.5 h and poured into water (1 L). The layers are separated and the organic layer washed with brine, dried (sodium sulfate), filtered, and concentrated in vacuo to yield 4-chloro-butyric acid benzhydrylidene-hydrazide as a residue.

Workup

  1. temperaturea gentle reflux throughout the addition
  2. customThe layers are separated
  3. washthe organic layer washed with brine
  4. dry with materialdried (sodium sulfate)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6e9f813cdbf440e28165af869bd6f9f1
Source dataset
uspto-grants-2006_08
Patent number
US07087626B2

Linked notes

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