Glyoxal → HCID 178442959, compound

HRID 374729

Reaction equation

HRID 374729 reaction equation
[C:1]1([CH3:12])[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[N:8]=[N:9][NH:10][CH:11]=1.[CH2:13]([NH2:31])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20]/[CH:21]=[CH:22]\[CH2:23]CCCCCCC.C(C=O)=O.[C:36]([OH:55])(=[O:54])[CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43]/[CH:44]=[CH:45]\[CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH3:53]>C1(C)C=CC=CC=1.C(O)C>[C:48]1([CH3:47])[CH:49]=[CH:50][CH:51]=[CH:52][C:53]=1[NH:31][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20]/[CH:21]=[CH:22]\[CH2:23][CH2:12][CH2:1][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][C:7]1[N:8]=[N:9][NH:10][CH:11]=1.[C:36]([OH:55])(=[O:54])[CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43]/[CH:44]=[CH:45]\[CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH3:53]

Participants

7

Reactant 4

HCID 7860GlyoxalHCID 445639Oleic AcidHCID 5356789OleylamineHCID 178424185HCID 178424185, compound

Product 1

HCID 178442959HCID 178442959, compoundYield 343.6%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 1140TolueneSolvent

Procedure

Approximately 53 grams (0.4 mole) tolyltriazole, 111 grams (0.4 mole) oleyl amine, 100 ml ethanol, and 100 ml toluene were charged to a 1 liter flask equipped with an agitator, Dean-Stark apparatus, and dropping funnel. This mixture was stirred to a homogeneous mixture. Glyoxal (29 grams, 0.2 mole, 40% in water) was added dropwise and then stirred at room temperature for 12 hours. Water was then azeotropically removed by heating to reflux temperatures of approximately 100°-120° C. While maintaining a temperature of less than or equal to 60° C., 56 grams (0.2 mole) oleic acid was added slowly. The reaction mixture was stirred at 60° C. for 1 hour. The orange product (243 grams) was isolated by filtration and removal of solvent under reduced pressure.

Workup

  1. customequipped with an agitator, Dean-Stark apparatus
  2. stirringstirred at room temperature for 12 hours
  3. customWater was then azeotropically removed
  4. temperatureby heating
  5. temperatureto reflux temperatures of approximately 100°-120° C
  6. additionwas added slowly
  7. stirringThe reaction mixture was stirred at 60° C. for 1 hour

Sources & evidence

ORD record
ord-0425997ffab44149954102049b772173
Source dataset
uspto-grants-1996_01
Patent number
US05482521

Linked notes

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