Triethyl phosphite → 2,3-Bis(difluoroamino)propyl prop-2-enoate

HRID 917921Notes

Reaction equation

HRID 917921 reaction equation
C(OP(OCC)OCC)C.Br[CH:12]([CH2:25]Br)[C:13]([O:15][CH2:16][CH:17]([N:22]([F:24])[F:23])[CH2:18][N:19]([F:21])[F:20])=[O:14]>C1C=CC=CC=1>[C:13]([O:15][CH2:16][CH:17]([N:22]([F:23])[F:24])[CH2:18][N:19]([F:21])[F:20])(=[O:14])[CH:12]=[CH2:25]

Participants

4

Reactant 2

HCID 31215Triethyl phosphiteHCID 21524287HCID 21524287, compound

Product 1

HCID 224651592,3-Bis(difluoroamino)propyl prop-2-enoateYield 30%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

Employing a system similar to that of Example 1, 7.30 parts (0.044 mole) of triethylphosphite is added to a solution of 16.5 parts (0.044 mole) of 2,3-bis(difluoramino)-propyl α,β-dibromopropionate in 100 ml. of dry benzene. The addition is made over a period of 30 minutes. A slightly exothermic reaction (25° to 36° C.) is observed. The mixture is stirred at ambient temperature for 24 hours, freed of solvent and distilled to give 2.89 parts (30 percent) of 2,3-bis(difluoramino)propyl acrylate (b.p. 42° C., 0.45 mm. of mercury). The product conforms to the known 2,3-bis(difluoramino)propyl acrylate. The product gives the following analysis:

Workup

  1. additionThe addition
  2. customA slightly exothermic reaction (25° to 36° C.)
  3. distillationdistilled

Sources & evidence

ORD record
ord-4b1f2952841d4a018f70a79c52c1c8fe
Source dataset
uspto-grants-1976_07
Patent number
US03968150

Reaction notes

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