Ammonia → HCID 21411399, compound
Reaction equation
[NH3:1].C[O:3][C:4]([P:6](=[O:15])([O:11][CH2:12][CH:13]=[CH2:14])[O:7][CH2:8][CH:9]=[CH2:10])=O>O1CCCC1>[C:4]([P:6](=[O:15])([O:11][CH2:12][CH:13]=[CH2:14])[O:7][CH2:8][CH:9]=[CH2:10])(=[O:3])[NH2:1]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 35 °C
Procedure
A slight excess (5-10%) of gaseous ammonia is introduced into a stirring mixture of 11 parts of diallyl methoxycarbonylphosphonate (from triallyl phosphite and methyl chloroformate) and 200 parts of tetrahydrofuran. The temperature increases from 25° to 28° C. spontaneously. The mixture is then heated to 35° C. and maintained at this temperature for 2 hours. The slightly hazy solution is filtered, and solvent is removed from the filtrate at 50° C. under reduced pressure (15 mm.). The residual solid is recrystallized from benzene, giving 6 parts of white crystalline diallyl carbamoylphosphonate, m.p. 91°-94° C.
Workup
- temperatureThe temperature increases from 25° to 28° C. spontaneously
- temperaturemaintained at this temperature for 2 hours
- filtrationThe slightly hazy solution is filtered
- customsolvent is removed from the filtrate at 50° C. under reduced pressure (15 mm.)
- customThe residual solid is recrystallized from benzene
Sources & evidence
- ORD record
- ord-d171b4e053ee49089dc211533dd5d293
- Source dataset
- uspto-grants-1977_04
- Patent number
- US04017297
Reaction notes
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