1,3-Dibromo-2-propanol → 2-Hydroxy-1,3-bis(7,7,8,9,9-pentamethyl-2,4-dioxo-1,3,8-triazaspiro[4.5]dec-3-yl)propane

HRID 972026Notes

Reaction equation

HRID 972026 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+].Br[CH2:21][CH:22]([OH:25])[CH2:23]Br>CN(C)C=O>[OH:25][CH:22]([CH2:23][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])[CH2:21][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 72871,3-Dibromo-2-propanolHCID 14797Potassium HydroxideHCID 204818537,7,8,9,9-Pentamethyl-1,3,8-triazaspiro[4.5]decane-2,4-dione

Product 1

HCID 203968002-Hydroxy-1,3-bis(7,7,8,9,9-pentamethyl-2,4-dioxo-1,3,8-triazaspiro[4.5]dec-3-yl)propane

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

22.0 g of 7,7,8,9,9-pentamethyl-1,3,8-triazaspiro[4.5]decane-2,4-dione and 5.1 g of potassium hydroxide were added to 200 ml of N,N-dimethylformamide, and the mixture was heated, with stirring, for 30 minutes at 50°-60° C. At the end of this time, 9.0 g of 1,3-dibromo-2-propanol were added dropwise to the mixture and the whole mixture was heated, with stirring, for 6 hours at 100°-110° C. After completion of the reaction, the reaction mixture was condensed by evaporation and the residue was washed with a 1% w/w aqueous solution of potassium hydroxide and then recrystallised from a 2:1 by volume mixture of benzene and ethanol, giving the desired Compound No. 164 in the form of white crystals, melting point 255°-256° C.

Workup

  1. temperaturethe mixture was heated
  2. temperaturethe whole mixture was heated
  3. stirringwith stirring, for 6 hours at 100°-110° C
  4. customAfter completion of the reaction
  5. customcondensed
  6. customby evaporation
  7. washthe residue was washed with a 1% w/w aqueous solution of potassium hydroxide
  8. customrecrystallised from a 2:1 by volume mixture of benzene and ethanol

Sources & evidence

ORD record
ord-36a47f788e7a4837829d7d7712163d13
Source dataset
uspto-grants-1979_07
Patent number
US04162246

Reaction notes

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