Reaction #8300

Reaction equation

water

4-Chlorobutyryl chloride

benzophenone hydrazone

pyridine

→

4-chloro-butyric acid benzhydrylidene-hydrazide

Solvents

dichloromethane

Conditions

Workup

1. 1
   Temperaturea gentle reflux throughout the addition
2. 2
   OtherThe layers are separated
3. 3
   Washthe organic layer washed with brine
4. 4
   Dryingdried (sodium sulfate)
5. 5
   Filtrationfiltered
6. 6
   Concentrationconcentrated in vacuo

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.

Source