Ammonia → HCID 13273295, compound

HRID 2072209Notes

Reaction equation

HRID 2072209 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[N:15]1[C:19]([CH2:20][Cl:21])=[N:18][C:17]([C:22](O)=[O:23])=[N:16]1)=[O:8].C(Cl)(Cl)Cl.C(Cl)(=O)OCC.[NH3:35]>C(N(CC)CC)C>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[N:15]1[C:19]([CH2:20][Cl:21])=[N:18][C:17]([C:22]([NH2:35])=[O:23])=[N:16]1)=[O:8]

Participants

6

Reactant 4

HCID 222AmmoniaHCID 6212ChloroformHCID 10928Ethyl chloroformateHCID 13273294HCID 13273294, compound

Product 1

HCID 13273295HCID 13273295, compound

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

To a solution of 0.258 g. of 1-[2-(2-pyridinecarbonyl)phenyl]-5-chloromethyl-1H-1,2,4-triazole-3-carboxylic acid in 7.5 ml. of chloroform are added 0.14 ml. of triethylamine and then 0.1 ml. of ethyl chlorocarbonate with ice-cooling. After stirring for 10 minutes, to the resulting mixture is added 0.5 ml. of concentrated aqueous ammonia, and the whole mixture is further stirred for 30 minutes. The precipitated crystals are collected by filtration, washed successively with water, ethanol and ether, and then dried to give 1-[2-(2-pyridinecarbonyl)phenyl]-5-chloromethyl-1H-1,2,4-triazole-3-carboxamide as crystals. The filtrate is extracted with chloroform and the chloroform layer is washed with water, dried over sodium sulfate, followed by evaporation of the solvent to give additional crystals identical with the abovementioned crystals. Recrystallization of the combined crystals from chloroform-ethanol gives colorless needles, melting at 228° to 229° C. (decomposition).

Workup

  1. additionis added 0.5 ml
  2. filtrationThe precipitated crystals are collected by filtration
  3. washwashed successively with water, ethanol and ether
  4. customdried

Sources & evidence

ORD record
ord-6da33c2c11b4443db8ee4fff1550dea3
Source dataset
uspto-grants-1977_09
Patent number
US04049812

Reaction notes

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