Potassium Hydroxide → Ethylene glycol bis[2hydroxy-3-(7,7,8,9,9-pentamethyl-2,4-dioxo-1,3,8-triazaspiro[4.5]dec-3-yl)propyl]ether

HRID 1648797Notes

Reaction equation

HRID 1648797 reaction equation
[CH3:1][C:2]1([CH3:17])[N:13]([CH3:14])[C:12]([CH3:16])([CH3:15])[CH2:11][C:4]2([NH:8][C:7](=[O:9])[NH:6][C:5]2=[O:10])[CH2:3]1.[OH-:18].[K+].[O:20]1[CH2:31][CH:21]1[CH2:22][O:23][CH2:24][CH2:25][O:26][CH2:27][CH:28]1[O:30][CH2:29]1>CO>[OH:20][CH:21]([CH2:31][N:6]1[C:5](=[O:18])[C:4]2([CH2:3][C:2]([CH3:1])([CH3:17])[N:13]([CH3:14])[C:12]([CH3:16])([CH3:15])[CH2:11]2)[NH:8][C:7]1=[O:9])[CH2:22][O:23][CH2:24][CH2:25][O:26][CH2:27][CH:28]([OH:30])[CH2:29][N:6]1[C:5](=[O:10])[C:4]2([CH2:3][C:2]([CH3:17])([CH3:1])[N:13]([CH3:14])[C:12]([CH3:16])([CH3:15])[CH2:11]2)[NH:8][C:7]1=[O:9]

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 16683Glycol diglycidyl etherHCID 204818537,7,8,9,9-Pentamethyl-1,3,8-triazaspiro[4.5]decane-2,4-dione

Product 1

HCID 131711583Ethylene glycol bis[2hydroxy-3-(7,7,8,9,9-pentamethyl-2,4-dioxo-1,3,8-triazaspiro[4.5]dec-3-yl)propyl]ether

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To 60 ml of methanol were added 10.0 g of 7,7,8,9,9-pentamethyl-1,3,8-triazaspiro[4.5]decane-2,4-dione, 0.1 g of potassium hydroxide and 3.0 g of ethyleneglycol bis(2,3-epoxypropyl)ether and the mixture was refluxed for 8 hours, under stirring. After completion of the reaction, the reaction mixture was cooled and crystals precipitated were washed with methanol and recrystallized from benzene, giving the desired compound as white crystals melting at 213°-215° C. Referential Example 2.

Workup

  1. temperaturethe mixture was refluxed for 8 hours
  2. customAfter completion of the reaction
  3. temperaturethe reaction mixture was cooled
  4. customcrystals precipitated
  5. washwere washed with methanol
  6. customrecrystallized from benzene

Sources & evidence

ORD record
ord-99cb61ae41c54dfebb81e8c0e963d865
Source dataset
uspto-grants-1983_11
Patent number
US04413076

Reaction notes

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