Acetic Acid → HCID 86736118, compound

HRID 1112494Notes

Reaction equation

HRID 1112494 reaction equation
[OH2:1].[CH2:2]([N:4]([CH2:26][CH3:27])[CH2:5][CH2:6][NH:7][C:8]([C:10]1NC(C2C=CC=CC=2)=[C:13]2[C:18]=1[CH:17]=[CH:16][C:15]([Cl:19])=[CH:14]2)=[O:9])[CH3:3].[C:28]([OH:31])(=O)[CH3:29]>>[ClH:19].[CH2:26]([N:4]([CH2:2][CH3:3])[CH2:5][CH2:6][NH:7][C:8](=[O:9])[C:10]([C:18]1[CH:17]=[CH:16][C:15]([C:28](=[O:31])[C:29]2[CH:10]=[CH:18][CH:13]=[CH:14][CH:15]=2)([Cl:19])[CH2:14][CH:13]=1)=[O:1])[CH3:27]

Participants

4

Reactant 3

HCID 176Acetic AcidHCID 962WaterHCID 54536393HCID 54536393, compound

Product 1

HCID 86736118HCID 86736118, compound

Conditions

Temperature
80 °C

Procedure

86.4 G. of ceric ammonium nitrate are dissolved in 150 ml. of water and 150 ml. of glacial acetic acid. 22.2 G. of 5-chloro-3-phenylisoindole-1-carboxylic acid [2-(diethylamino)ethyl]amide are added and the mixture is stirred at 80° C. for 20 minutes, the color of the solution obtained changing from orange to light yellow. After cooling, 750 ml. of ice-water are added and the separated oil is extracted with methylene chloride. The extract is washed with 2-N ammonium hydroxide and a saturated sodium chloride solution, dried over sodium sulfate and evaporated. The oily residue is dissolved in diethyl ether and treated with excess ethereal hydrochloric acid. The precipitated hydrochloride is removed by filtration, washed with diethyl ether and dried over phosphorus pentoxide in a desiccator. After recrystallization from methylene chloride/diethyl ether, there is obtained p-benzoyl-p-chlorophenylglyoxylic acid [2-(diethylamino)ethyl]amide hydrochloride in the form of almost colorless crystals having a melting point of 161°-164° C. (decomposition).

Workup

  1. customthe color of the solution obtained
  2. temperatureAfter cooling
  3. extractionthe separated oil is extracted with methylene chloride
  4. washThe extract is washed with 2-N ammonium hydroxide
  5. dry with materiala saturated sodium chloride solution, dried over sodium sulfate
  6. customevaporated
  7. dissolutionThe oily residue is dissolved in diethyl ether
  8. additiontreated with excess ethereal hydrochloric acid
  9. customThe precipitated hydrochloride is removed by filtration
  10. washwashed with diethyl ether
  11. dry with materialdried over phosphorus pentoxide in a desiccator
  12. customAfter recrystallization from methylene chloride/diethyl ether

Sources & evidence

ORD record
ord-0a6841ad83934d269b554e0e63f06d4c
Source dataset
uspto-grants-1978_10
Patent number
US04122265

Reaction notes

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