Ethylamine → HCID 20333051, compound

HRID 1707004Notes

Reaction equation

HRID 1707004 reaction equation
[Cl:1][C:2]1[CH:26]=[CH:25][CH:24]=[CH:23][C:3]=1[C:4]([C:6]1[CH:11]=[C:10]([Cl:12])[CH:9]=[CH:8][C:7]=1[N:13]1[C:17]([CH2:18][Cl:19])=[N:16][C:15]([C:20](Cl)=[O:21])=[N:14]1)=[O:5].[CH2:27]([NH2:29])[CH3:28]>O1CCOCC1>[CH2:27]([NH:29][C:20]([C:15]1[N:16]=[C:17]([CH2:18][Cl:19])[N:13]([C:7]2[CH:8]=[CH:9][C:10]([Cl:12])=[CH:11][C:6]=2[C:4](=[O:5])[C:3]2[CH:23]=[CH:24][CH:25]=[CH:26][C:2]=2[Cl:1])[N:14]=1)=[O:21])[CH3:28]

Participants

4

Reactant 2

HCID 6341EthylamineHCID 20333049HCID 20333049, compound

Product 1

HCID 20333051HCID 20333051, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

The resulting crude 1-[2-(o-chlorobenzoyl)-4-chlorophenyl]-5-(chloromethyl)-1H-1,2,4-triazole-3-carbonyl chloride is dissolved in 80 ml of dioxane, and to the solution is added dropwise at room temperature, in the course of 30 minutes, a solution of 1.98 g (0.044 mole) of ethylamine in 30 ml of dioxane. The ethylamine hydrochloride gradually precipitates out. The reaction mixture is concentrated in vacuo to dryness. Ice water and ether are added to the residue; the organic phase is separated and is washed successively with cold 1 N hydrochloric acid, with cold 0.1 N sodium hydroxide solution and with saturated sodium chloride solution. After drying, and concentration in vacuo, is obtained crude N-ethyl-1-[2-(o-chlorobenzoyl)-4-chlorophenyl]-5-(chloromethyl)-1H-1,2,4-triazole-3-carboxamide.

Workup

  1. additionto the solution is added dropwise at room temperature, in the course of 30 minutes
  2. customThe ethylamine hydrochloride gradually precipitates out
  3. concentrationThe reaction mixture is concentrated in vacuo to dryness
  4. additionIce water and ether are added to the residue
  5. customthe organic phase is separated
  6. washis washed successively with cold 1 N hydrochloric acid, with cold 0.1 N sodium hydroxide solution and with saturated sodium chloride solution
  7. customAfter drying
  8. concentrationconcentration in vacuo

Sources & evidence

ORD record
ord-b169808bb90440dcb090af79ba35872f
Source dataset
uspto-grants-1980_06
Patent number
US04209516

Reaction notes

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