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

HRID 1788330Notes

Reaction equation

HRID 1788330 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>C(Cl)Cl>[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 CH2Cl2 (520 mL) under nitrogen at a rate that maintained 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 is washed with brine, dried (Na2SO4), filtered, and concentrated in vacuo to yield 4-chloro-butyric acid benzhydrylidene-hydrazide as a residue.

Workup

  1. temperaturethat maintained
  2. temperaturea gentle reflux throughout the addition
  3. customThe layers are separated
  4. washthe organic layer is washed with brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-34c2f1a97cd04a1eb04c0d7754254a54
Source dataset
uspto-grants-2009_03
Patent number
US07511065B2

Reaction notes

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