Diketene → benzyl N-(2-acetoacetamidoethyl)carbamate

HRID 67740Notes

Reaction equation

HRID 67740 reaction equation
[NH2:1][CH2:2][CH2:3][NH:4][C:5](=[O:14])[O:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[CH2:15]=[C:16]1[O:20][C:18](=[O:19])[CH2:17]1>CCOCC>[C:18]([NH:1][CH2:2][CH2:3][NH:4][C:5](=[O:14])[O:6][CH2:7][C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)(=[O:19])[CH2:17][C:16]([CH3:15])=[O:20]

Participants

4

Reactant 2

HCID 12661DiketeneHCID 2794257Benzyl N-(2-aminoethyl)carbamate

Product 1

HCID 20467080benzyl N-(2-acetoacetamidoethyl)carbamateYield 90%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent3×

Procedure

A solution of benzyl N-(2-aminoethyl)carbamate (54 g, 0.276 mole) in ether (250 ml) and a solution of diketene (25.2 g, 0.30 mole) in ether (250 ml) were added simultaneously, dropwise, to ether (600 ml) while stirring and cooling over a 30 minute period. A white precipitate appeared. The solution was stirred 30 minutes longer, and then filtered. One recrystallization from water gave pure benzyl N-(2-acetoacetamidoethyl)carbamate (m.p.=116°-118° C.) at a yield of 90%.

Workup

  1. temperaturecooling over a 30 minute period
  2. filtrationfiltered
  3. customOne recrystallization from water

Sources & evidence

ORD record
ord-c56707b35a1745ce966752d44a88fba8
Source dataset
uspto-grants-1982_08
Patent number
US04346231

Reaction notes

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