Triethylamine hydrochloride → HCID 22167082, compound

HRID 621597Notes

Reaction equation

HRID 621597 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH:7][NH2:8].Cl[CH2:10][C:11]([CH3:16])([CH3:15])[C:12](Cl)=[O:13].Cl.C(N(CC)CC)C>ClCCl.C(N(CC)CC)C>[CH3:10][C:11]1([CH3:16])[CH2:15][N:7]([C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=2)[NH:8][C:12]1=[O:13]

Participants

6

Reactant 3

HCID 11130Triethylamine hydrochlorideHCID 613453-Chloro-2,2-dimethylpropanoyl chlorideHCID 786452-Hydrazinopyridine

Product 1

HCID 22167082HCID 22167082, compoundYield 71.2%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8471TriethylamineSolvent

Procedure

2-Pyridylhydrazine (10.9 g) in dichloromethane (120 ml) and dry triethylamine (28 ml) were chilled in an ice bath. -β-chloropivaloyl chloride (15.5 g) in dichloromethane (20 ml) was added dropwise with stirring for 15 minutes and the mixture was refluxed for 3 hours. When cool the triethylamine hydrochloride was filtered off and the filtrate evaporated to dryness and rinsed four times with the minimum quantity of ether to give the title compound (13.6 g) after recrystallisation from cyclohexane mp 141°-144°.

Workup

  1. temperaturethe mixture was refluxed for 3 hours
  2. filtrationwas filtered off
  3. customthe filtrate evaporated to dryness
  4. washrinsed four times with the minimum quantity of ether

Sources & evidence

ORD record
ord-e7c363d37e0f4ccabd78f2c9f5bf69c8
Source dataset
uspto-grants-1989_04
Patent number
US04824859

Reaction notes

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