Ethylene Glycol → HCID 19974704, compound

HRID 1451505Notes

Reaction equation

HRID 1451505 reaction equation
[CH2:1]([OH:4])[CH2:2][OH:3].CC(C)([O-])C.[K+].Cl[CH2:12][C:13]([N:15]([CH2:22][CH:23]([CH3:25])[CH3:24])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:14].O>CN(C=O)C>[OH:3][CH2:2][CH2:1][O:4][CH2:12][C:13]([N:15]([CH2:22][CH:23]([CH3:25])[CH3:24])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:14]

Participants

6

Reactant 4

HCID 174Ethylene GlycolHCID 962WaterHCID 19974702HCID 19974702, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 19974704HCID 19974704, compoundYield 99.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of ethylene glycol (12.4 g, 200 mmol) in DMF (50 ml) was carefully added potassium tert-butoxide (16.8 g, 150 mmol) while the temperature was kept below 70° C. The resulting mixture was stirred at ambient temperature for 30 min, then a solution of the above acetamide (11.3 g, 50 mmol) in DMF (5 ml) was added in one portion and the mixture was stirred at room temperature for 1.5 h. The reaction mixture was poured into iced water (400 ml) and extracted with dichloromethane (2×50 ml). The combined organic phases were dried (MgSO4) and the solvent was evaporated in vacuo to give 12.5 g of 2-(2-hydroxyethoxy)-N-(2-methyl-1-propyl)-N-phenylacetamide.

Workup

  1. customwas kept below 70° C
  2. stirringthe mixture was stirred at room temperature for 1.5 h
  3. extractionextracted with dichloromethane (2×50 ml)
  4. dry with materialThe combined organic phases were dried (MgSO4)
  5. customthe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-b7f7dc71b7494f9eb7379e60887b482e
Source dataset
uspto-grants-1997_02
Patent number
US05604242

Reaction notes

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