Pyridine → 2-Chloroethyl 2-(2,6-dimethylphenyl)-hydrazinecarboxylate

HRID 1903404Notes

Reaction equation

HRID 1903404 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[NH:9][NH2:10].N1C=CC=CC=1.[Cl:17][CH2:18][CH2:19][O:20][C:21](Cl)=[O:22]>O>[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[NH:9][NH:10][C:21]([O:20][CH2:19][CH2:18][Cl:17])=[O:22]

Participants

5

Reactant 3

HCID 1049PyridineHCID 123052-Chloroethyl chloroformateHCID 408103(2,6-Dimethylphenyl)hydrazine

Product 1

HCID 130364932-Chloroethyl 2-(2,6-dimethylphenyl)-hydrazinecarboxylate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 127 g (0.935 mol) 2,6-dimethylphenylhydrazine, 102.5 g (1.3 mol) pyridine and 400 ml water is added, at 0°-5°, 133.5 g (0.935 mol) chloroformic acid β-chloroethyl ester. After the addition is complete, the mixture is stirred for 2 hours at room temperature, the formed precipitate filtered off, washed with water and dried. The so obtained title compound is recrystallised from toluene to yield colourless crystals, m.p. 74°-75°.

Workup

  1. additionis added, at 0°-5°
  2. additionAfter the addition
  3. filtrationthe formed precipitate filtered off
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-ef559cddc4d545e6b7435c82beb3035a
Source dataset
uspto-grants-1984_03
Patent number
US04436744

Reaction notes

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