Ethylene Oxide → HCID 54110719, compound
Reaction equation
[CH2:1]1[O:3][CH2:2]1.[CH3:4][CH:5]([CH3:23])[CH2:6][CH:7]([N:16]1[C:20](=[O:21])[NH:19][NH:18][C:17]1=[O:22])[CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[CH3:24][C:25](N(C)C)=[O:26]>[OH-].C[N+](C)(C)CC1C=CC=CC=1>[OH:26][CH2:25][CH2:24][N:19]1[C:20](=[O:21])[N:16]([CH:7]([CH2:6][CH:5]([CH3:23])[CH3:4])[CH2:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:17](=[O:22])[N:18]1[CH2:2][CH2:1][OH:3]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
26.4 g of ethylene oxide are introduced into 82.5 g of 4-(5-methyl-1-phenyl-3-hexyl)-1,2,4-triazolidine-3,5-dione (starting material 9) and 0.3 g of trimethyl benzyl ammonium hydroxide in 150 g of dimethyl acetamide. The solvent is distilled off in vacuo, the residue is dissolved by heating in 150 ml of ethyl acetate, 10 g of powdered active carbon are added and the whole is filtered hot. A deposit crystallises out on cooling and is isolated by filtration under suction and dried, giving 68 g of 1,2-bis-(2-hydroxyethyl)-4-(5-methyl-1-phenyl-3-hexyl)-1,2,4-triazolidine-3,5-dione in the form of colourless crystals melting at 114° C. IR- and NMR-spectra together with elemental analysis confirm the assumed structure.
Workup
- distillationThe solvent is distilled off in vacuo
- dissolutionthe residue is dissolved
- temperatureby heating in 150 ml of ethyl acetate
- addition10 g of powdered active carbon are added
- filtrationthe whole is filtered hot
- customA deposit crystallises out
- temperatureon cooling
- customis isolated by filtration under suction
- customdried
Sources & evidence
- ORD record
- ord-f6b7cced724a47b08092dfd7b9d11f05
- Source dataset
- uspto-grants-1983_03
- Patent number
- US04377694
Reaction notes
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