Formic Acid → ethyl N-(but-2-enyl)-N-(2-oxoethyl)-carbamate

HRID 2255721Notes

Reaction equation

HRID 2255721 reaction equation
[CH2:1]([N:5]([CH2:11][CH:12](OC)[O:13]C)[C:6](=[O:10])[O:7][CH2:8][CH3:9])[CH:2]=[CH:3][CH3:4].C(O)=O.[Cl-].[Na+]>O>[CH2:1]([N:5]([CH2:11][CH:12]=[O:13])[C:6](=[O:10])[O:7][CH2:8][CH3:9])[CH:2]=[CH:3][CH3:4]

Participants

5

Reactant 3

HCID 284Formic AcidHCID 5234Sodium ChlorideHCID 54206204Ethyl N-(2-buten-1-yl)-N-(2,2-dimethoxyethyl)-carbamate

Product 1

HCID 53690408ethyl N-(but-2-enyl)-N-(2-oxoethyl)-carbamate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

111 g (0.48 mol) of ethyl N-(2-buten-1-yl)-N-(2,2-dimethoxyethyl)-carbamate are heated under reflux for three hours with 50 g of formic acid in 950 ml of water. The mixture is saturated with sodium chloride and extracted three times using 200 ml of methylene chloride each time. The organic phases are washed with sodium hydrogen carbonate solution until neutral, dried over magnesium sulphate and concentrated, and the residue is distilled.

Workup

  1. extractionextracted three times
  2. washThe organic phases are washed with sodium hydrogen carbonate solution until neutral,
  3. dry with materialdried over magnesium sulphate
  4. concentrationconcentrated
  5. distillationthe residue is distilled

Sources & evidence

ORD record
ord-c50775727e6a47df87c24342d723093a
Source dataset
uspto-grants-1993_08
Patent number
US05241076

Reaction notes

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