Water → HCID 20330236, compound

HRID 2057751Notes

Reaction equation

HRID 2057751 reaction equation
[C:1](Cl)([C:3]([O:5][CH2:6][CH3:7])=[O:4])=[O:2].[CH3:9][C:10]1[CH:11]=[C:12]([CH:17]=[C:18]([CH3:20])[CH:19]=1)[C:13]([NH:15][NH2:16])=[O:14].C(N(CC)CC)C.O>O1CCOCC1>[C:1]([NH:16][NH:15][C:13](=[O:14])[C:12]1[CH:17]=[C:18]([CH3:20])[CH:19]=[C:10]([CH3:9])[CH:11]=1)([C:3]([O:5][CH2:6][CH3:7])=[O:4])=[O:2]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 20884Ethoxalyl chlorideHCID 38583463,5-dimethylbenzohydrazide

Product 1

HCID 20330236HCID 20330236, compoundYield 70.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

265 g of ethoxalyl chloride are added, in the course of one hour, to 316 g of 3,5-dimethylbenzhydrazide and 195 g of triethylamine in 1.58 liters of anhydrous dioxane, whilst keeping the temperature of the reaction medium at about 10°-12° C. The stirring is continued (sic) for about two hours. whilst allowing the temperature to return to the ambient value. The reaction mixture is then poured into seven liters of water, whilst stirring. The precipitate which has formed is filtered off, washed three times with one liter of water and then dried at 20° C. under a pressure of one millimeter of mercury. 357 g of 1-ethoxalyl-2-(3,5-dimethylbenzoyl)-hydrazine, which melts at 159° C., are obtained.

Workup

  1. customat about 10°-12° C
  2. customfor about two hours
  3. customThe precipitate which has formed
  4. filtrationis filtered off
  5. washwashed three times with one liter of water
  6. customdried at 20° C. under a pressure of one millimeter of mercury

Sources & evidence

ORD record
ord-2ff9f955193244c7875382a7bc874e96
Source dataset
uspto-grants-1980_07
Patent number
US04212867

Reaction notes

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