Ethanol → HCID 178442904, compound

HRID 1735635Notes

Reaction equation

HRID 1735635 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(O)C.C(C=O)=O>C1(C)C=CC=CC=1>[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]

Participants

6

Reactant 4

HCID 702EthanolHCID 7860GlyoxalHCID 6435904N-Oleyl-1,3-propanediamineHCID 178424185HCID 178424185, compound

Product 1

HCID 178442904HCID 178442904, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
150 °C

Procedure

Approximately 66.6 grams (0.5 mole) tolyltriazole, 175 grams (0.5 mole) N-oleyl-1,3-diaminopropane (Armak Chemical Co.), 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 (36.3 grams, 0.25 mole, 40% in water) was added dropwise and then stirred at room temperature for 12 hours. Water was then azeotropically removed by heating to 150° C. The orange product (237 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

Sources & evidence

ORD record
ord-631298cd51fc46a7a9bfc85b4b6d0063
Source dataset
uspto-grants-1996_07
Patent number
US05538653

Reaction notes

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