Triethylamine → HCID 12948260, compound

HRID 1283423Notes

Reaction equation

HRID 1283423 reaction equation
[C:1]1([O-:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Na+].Cl[C:10]([N:12]1[CH2:16][CH2:15][NH:14][C:13]1=[O:17])=[O:11].C(N(CC)CC)C.[OH-].[Na+]>O1CCCC1.O>[O:7]([C:10]([N:12]1[CH2:16][CH2:15][NH:14][C:13]1=[O:17])=[O:11])[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

7

Reactant 4

HCID 8471Triethylamine2×HCID 14798Sodium HydroxideHCID 832412-Oxoimidazolidine-1-carbonyl chlorideHCID 4445035Phenolate Sodium

Product 1

HCID 12948260HCID 12948260, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

12.7 parts by weight of sodium phenolate were dissolved in 120 parts by volume of 80% strength tetrahydrofurane and the solution was adjusted to pH = 8. 14.9 parts by weight of N-chlorocarbonyl-imidazolid-2-one were now introduced while stirring and keeping the pH value constant at 8 by simultaneous addition of triethylamine. The mixture was further stirred until the pH remained constant even without addition of triethylamine. 100 parts by volume of water were now added, the tetrahydrofurane was stripped off in vacuo, the residue was adjusted to pH = 10 with sodium hydroxide solution, and the solution was extracted with ethyl acetate. The organic solution was washed with water, dried over MgSO4 and evaporated and the residue was dried under an oil pump at 60°C for 1 hour and recrystallized from acetone.

Workup

  1. stirringThe mixture was further stirred until the pH
  2. extractionthe solution was extracted with ethyl acetate
  3. washThe organic solution was washed with water
  4. dry with materialdried over MgSO4
  5. customevaporated
  6. customthe residue was dried under an oil pump at 60°C for 1 hour
  7. customrecrystallized from acetone

Sources & evidence

ORD record
ord-52799f7f97ef40858fb48ea816eef2c7
Source dataset
uspto-grants-1976_08
Patent number
US03975375

Reaction notes

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