ethyl N-carbonylcarbamate → ethyl N-diethoxyphosphorylcarbonylcarbamate

HRID 441899

Reaction equation

HRID 441899 reaction equation
[CH2:1]([O:3][P:4]([O-:8])[O:5][CH2:6][CH3:7])[CH3:2].[CH2:9]([O:11][C:12]([N:14]=[C:15]=[O:16])=[O:13])[CH3:10]>C(N(CC)CC)C.C(Cl)Cl>[CH2:1]([O:3][P:4]([C:15]([NH:14][C:12](=[O:13])[O:11][CH2:9][CH3:10])=[O:16])([O:5][CH2:6][CH3:7])=[O:8])[CH3:2]

Participants

5

Reactant 2

HCID 300166ethyl N-carbonylcarbamateHCID 3780918Diethylphosphite

Product 1

HCID 21415674ethyl N-diethoxyphosphorylcarbonylcarbamate

Reagents, catalysts & solvents 2

HCID 8471TriethylamineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 11.0 parts of diethylphosphite in 175 parts of methylene chloride and 4 drops of triethyl amine was added 10.0 parts of ethoxycarbonyl isocyanate. The solution was refluxed for 3 hours. Removing the solvent under reduced pressure left 18.5 parts of colorless oil which partially crystallized. The crystals were washed with cyclohexane to give 7.3 parts of ethyl N-(diethylphosphonocarbonyl)carbamate, m.p. 57°-64°, The proton nmr spectrum was consistent with this structure. (δNH = 10.0 ppm)

Workup

  1. temperatureThe solution was refluxed for 3 hours
  2. customRemoving the solvent under reduced pressure
  3. waitleft 18.5 parts of colorless oil which
  4. custompartially crystallized
  5. washThe crystals were washed with cyclohexane

Sources & evidence

ORD record
ord-56762ca4829e47c7a9e1d4357a3606d8
Source dataset
uspto-grants-1977_08
Patent number
US04043794

Linked notes

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