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Glycol diglycidyl ether → HCID 131712954, compound

HRID 1758204
Notes
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Reaction equation

HRID 1758204 reaction equation
[CH2:1]([N:13]1[C:17](=[O:18])[C:16]2([CH2:23][C:22]([CH3:25])([CH3:24])[NH:21][C:20]([CH3:27])([CH3:26])[CH2:19]2)[NH:15][C:14]1=[O:28])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].[O:29]1[CH2:40][CH:30]1[CH2:31][O:32][CH2:33][CH2:34][O:35][CH2:36][CH:37]1[O:39][CH2:38]1>C(O)CCCCCCC.C(OCC)(=O)C>[CH2:1]([N:13]1[C:17](=[O:18])[C:16]2([CH2:19][C:20]([CH3:27])([CH3:26])[N:21]([CH2:38][CH:37]([OH:39])[CH2:36][O:35][CH2:34][CH2:33][O:32][CH2:31][CH:30]([OH:29])[CH2:40][N:21]3[C:22]([CH3:25])([CH3:24])[CH2:23][C:16]4([NH:15][C:14](=[O:28])[N:13]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])[C:17]4=[O:18])[CH2:19][C:20]3([CH3:26])[CH3:27])[C:22]([CH3:25])([CH3:24])[CH2:23]2)[NH:15][C:14]1=[O:28])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 16683Glycol diglycidyl etherHCID 226228223-Dodecyl-7,7,9,9-tetramethyl-1,3,8-triazaspiro[4.5]decane-2,4-dione

Product 1

HCID 131712954HCID 131712954, compound

Reagents, catalysts & solvents 2

HCID 9571-OctanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
180 °C

Procedure

A mixture of 8.6 g of 3-dodecyl-7,7,9,9-tetramethyl-1,3,8-triazaspiro[4.5]decane-2,4-dione and 1.7 g of ethylene glycol bis(2,3-epoxypropyl)ether in 3 ml of octanol was heated to 180° C. for 30 hours. After completion of the reaction, the reaction mixture was dissolved in ethyl acetate and subjected to column chromatography through alumina eluted successively first with diethyl ether, second with a 10:1 by volume mixture of ethyl acetate and triethylamine, and lastly with methanol. The eluate eluted with the last solvent was separated and the solvent was removed therefrom by evaporation under reduced pressure, giving the desired Compound No. 355 in the form of white crystals melting at 74°-76° C.

Workup

  1. customAfter completion of the reaction
  2. washeluted successively first with diethyl ether, second with a 10:1 by volume mixture of ethyl acetate and triethylamine
  3. washThe eluate eluted with the last solvent
  4. customwas separated
  5. customthe solvent was removed
  6. customby evaporation under reduced pressure

Sources & evidence

ORD record
ord-cc78ed6783994bba8e01801e43aa8c19
Source dataset
uspto-grants-1983_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04371644

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes