Pyridine → HCID 53937327, compound

HRID 839301Notes

Reaction equation

HRID 839301 reaction equation
Cl.[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][NH2:10])=[CH:5][CH:4]=1.N1C=CC=CC=1.[C:17](Cl)(=[O:22])[C:18]([CH3:21])([CH3:20])[CH3:19]>O>[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]([C:17](=[O:22])[C:18]([CH3:21])([CH3:20])[CH3:19])[NH2:10])=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 62493Pivaloyl chlorideHCID 71600Hydrazine, (4-chlorophenyl)-, hydrochloride (1:1)

Product 1

HCID 53937327HCID 53937327, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

A quantity (25.0 g.; 0.14 mole) of (4-chlorophenyl)-hydrazine hydrochloride was suspended in 150 ml. of pyridine. The suspension was cooled to 0° C. and 16.9 g. (0.14 mole) of pivaloyl chloride was added with stirring. The reaction mixture was set aside at about 25° C. for 64 hrs. when 300 ml. of water was added. The precipitate that formed was collected on a filter and washed repeatedly with water, 1 N hydrochloric acid, and finally with water. The filter cake was dried under reduced pressure and 60° C. to remove water. After two recrystallizations from benzene and technical hexane there was thus obtained 24.1 g. of pivalic acid (4-chlorophenyl)hydrazide having a melting point of 137° to 138° C.

Workup

  1. customThe precipitate that formed
  2. customwas collected on
  3. filtrationa filter
  4. washwashed repeatedly with water, 1 N hydrochloric acid
  5. customThe filter cake was dried under reduced pressure and 60° C.
  6. customto remove water
  7. customAfter two recrystallizations from benzene and technical hexane

Sources & evidence

ORD record
ord-f57719d4b8dd41caaaecb7d50dba556c
Source dataset
uspto-grants-1978_06
Patent number
US04094906

Reaction notes

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