Carbamic acid, ethyl ester → Ethyl (3-oxobutanoyl)carbamate

HRID 1390129Notes

Reaction equation

HRID 1390129 reaction equation
[CH2:1]=[C:2]1[O:6][C:4](=[O:5])[CH2:3]1.[NH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9]>C(O)(=O)C>[C:8]([NH:7][C:4](=[O:5])[CH2:3][C:2]([CH3:1])=[O:6])([O:10][CH2:11][CH3:12])=[O:9]

Participants

4

Reactant 2

HCID 5641Carbamic acid, ethyl esterHCID 12661Diketene

Product 1

HCID 582816Ethyl (3-oxobutanoyl)carbamateYield 42.7%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of diketene (25 g), urethane (20 g), and acetic acid (75 ml) was refluxed for 25 minutes. Evaporation of the acetic acid under reduced pressure gave a syrup which crystallized on scratching. Recrystallization from benzene gave 16.6 g (32.5%) of N-carbethoxyacetoacetamide as colorless needles.

Workup

  1. temperaturewas refluxed for 25 minutes
  2. customEvaporation of the acetic acid under reduced pressure
  3. customgave a syrup which
  4. customcrystallized
  5. customRecrystallization from benzene

Sources & evidence

ORD record
ord-cf22466544634adc877fa2fb75ba53a4
Source dataset
uspto-grants-1981_01
Patent number
US04247712

Reaction notes

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