Sodium Carbonate → Benzyl 2,2-diethoxyethylcarbamate

HRID 2214808Notes

Reaction equation

HRID 2214808 reaction equation
C(=O)([O-])[O-].[Na+].[Na+].[C:7](Cl)([O:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:8].[CH2:18]([O:20][CH:21]([O:24][CH2:25][CH3:26])[CH2:22][NH2:23])[CH3:19]>C(OCC)(=O)C>[CH2:18]([O:20][CH:21]([O:24][CH2:25][CH3:26])[CH2:22][NH:23][C:7](=[O:8])[O:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH3:19]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 10387Benzyl chloroformateHCID 695242,2-Diethoxyethylamine

Product 1

HCID 292521Benzyl 2,2-diethoxyethylcarbamateYield 98%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

An aqueous solution (400 ml) of sodium carbonate (31.8 g) and carbobenzoxy chloride (51.2 g) were added to a solution of 2,2-diethoxyethylamine (42.0 g) in ethyl acetate (300 ml) under ice-cooling, and the mixture was stirred for 6 hours. After separating the mixture into layers, the organic layer was washed successively with 0.5N hydrochloric acid, an aqueous sodium bicarbonate solution and an aqueous saturated sodium chloride solution, dried and concentrated to give pale orange oily benzyl 2,2-diethoxyethylcarbamate (78.6 g).

Workup

  1. temperaturecooling
  2. customAfter separating the mixture into layers
  3. washthe organic layer was washed successively with 0.5N hydrochloric acid
  4. dry with materialan aqueous sodium bicarbonate solution and an aqueous saturated sodium chloride solution, dried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-0ee3da6ee7044ae8b974135809bb14d1
Source dataset
uspto-grants-2006_09
Patent number
US07109200B2

Reaction notes

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