Glyoxal → HCID 178442965, compound

HRID 1735637Notes

Reaction equation

HRID 1735637 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]([NH:31][CH2:32][CH2:33][CH2:34][NH2:35])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20]/[CH:21]=[CH:22]\[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30].C(C=O)=O.[C:40]([OH:59])(=[O:58])[CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47]/[CH:48]=[CH:49]\[CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH3:57]>C1(C)C=CC=CC=1.C(O)C>[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]([NH:31][CH2:32][CH2:33][CH2:34][NH2:35])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20]/[CH:21]=[CH:22]\[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30].[C:40]([OH:59])(=[O:58])[CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47]/[CH:48]=[CH:49]\[CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH3:57]

Participants

7

Reactant 4

HCID 7860GlyoxalHCID 445639Oleic AcidHCID 6435904N-Oleyl-1,3-propanediamineHCID 178424185HCID 178424185, compound

Product 1

HCID 178442965HCID 178442965, compoundYield 101.1%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 1140TolueneSolvent

Procedure

Approximately 53 grams (0.4 mole) tolyltriazole, 140 grams (0.4 mole) N-oleyl-1,3-diaminopropane, 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. After cooling to less than 60° C., 112 grams (0.4 mole) oleic acid was added slowly. The reaction mixture was stirred at 60° C. for 1 hour. The orange product (310 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. temperatureAfter cooling to less than 60° C.
  7. stirringThe reaction mixture was stirred at 60° C. for 1 hour

Sources & evidence

ORD record
ord-4600cdb9a8aa48168cdf63f88ef2d392
Source dataset
uspto-grants-1996_07
Patent number
US05538653

Reaction notes

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