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

HRID 1646021Notes

Reaction equation

HRID 1646021 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-4814db4d1e5a473bab282d92c13ff3c0
Source dataset
uspto-grants-1993_01
Patent number
US05177210

Reaction notes

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