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

HRID 1460792Notes

Reaction equation

HRID 1460792 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-e1e9ad2268824a1ab45c813e44b1ddb7
Source dataset
uspto-grants-1991_12
Patent number
US05071999

Reaction notes

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