Water → HCID 14032941, compound

HRID 986387Notes

Reaction equation

HRID 986387 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]2[CH:9]=[CH:8][C:7]([CH3:10])=[CH:6][N:5]2[C:11]=1[C:12]([NH:14][NH2:15])=[O:13].C(N(CC)CC)C.[Cl:23][CH2:24][C:25](Cl)=[O:26].O>C(Cl)(Cl)Cl>[Cl:23][CH2:24][C:25]([NH:15][NH:14][C:12]([C:11]1[N:5]2[CH:6]=[C:7]([CH3:10])[CH:8]=[CH:9][C:4]2=[N:3][C:2]=1[CH3:1])=[O:13])=[O:26]

Participants

6

Reactant 4

HCID 962WaterHCID 6577Chloroacetyl chlorideHCID 8471TriethylamineHCID 20157442HCID 20157442, compound

Product 1

HCID 14032941HCID 14032941, compoundYield 105.6%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

To a mixture of 14.8 g of 2,6-dimethylimidazo[1,2-a]pyridine-3-carbohydrazide and 7.36 g of triethylamine in 300 ml of chloroform with stirring under cooling is added dropwise a solution of 8 g of chloroacetyl chloride in 50 ml of chloroform at 5°-10° C. After the mixture is stirred for 30 minutes, the reaction temperature is raised to room temperature and the resultant mixture is further stirred for 30 minutes. To the reaction mixture is added water and the precipitated crystals are collected by filtration to give 21 g of N'-chloroacetyl-2,6-dimethylimidazo[1,2-a]pyridine-3-carbohydrazide, melting at 290°-291° C. with decomposition.

Workup

  1. temperatureunder cooling
  2. stirringAfter the mixture is stirred for 30 minutes
  3. filtrationthe precipitated crystals are collected by filtration

Sources & evidence

ORD record
ord-94a175f3cb80439ab86365f7a7d91fdb
Source dataset
uspto-grants-1987_12
Patent number
US04713381

Reaction notes

Loading…