Ethyl 3-amino-3-(4-chlorophenyl)propyl(diethoxymethyl)phosphinate → HCID 19379612, compound

HRID 542303Notes

Reaction equation

HRID 542303 reaction equation
[NH2:1][CH:2]([C:17]1[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=1)[CH2:3][CH2:4][P:5](C(OCC)OCC)(=[O:9])[O:6]CC>Cl>[NH2:1][CH:2]([C:17]1[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=1)[CH2:3][CH2:4][P:5]([OH:9])[OH:6]

Participants

3

Reactant 1

HCID 14362823Ethyl 3-amino-3-(4-chlorophenyl)propyl(diethoxymethyl)phosphinate

Product 1

HCID 19379612HCID 19379612, compound

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A solution of 10.5 g of ethyl 3-amino-3-(4-chlorophenyl)propyl(diethoxymethyl)phosphinate in 100 ml of 36% aqueous hydrochloric acid is heated to reflux for a period of 2 hours. The reaction mixture is then allowed to cool to room temperature, concentrated under reduced pressure, and co-evaporated twice with 25 ml of water under reduced pressure. The crude product is then dissolved in 20 ml of water, washed twice with 20 ml of diethyl ether and the aqueous layer is then separated and evaporated under reduced pressure. The crude product is dissolved in 50 ml of ethanol and 5 ml of propylene oxide is added dropwise. The precipitated solid is collected by filtration and dried to give 3-amino-3-(4-chlorophenyl)propylphosphonous acid, m.p. 284°-286° C., 31P=+27.2 ppm (D2O).

Workup

  1. temperatureto reflux for a period of 2 hours
  2. concentrationconcentrated under reduced pressure
  3. dissolutionThe crude product is then dissolved in 20 ml of water
  4. washwashed twice with 20 ml of diethyl ether
  5. customthe aqueous layer is then separated
  6. customevaporated under reduced pressure
  7. dissolutionThe crude product is dissolved in 50 ml of ethanol
  8. addition5 ml of propylene oxide is added dropwise
  9. filtrationThe precipitated solid is collected by filtration
  10. customdried

Sources & evidence

ORD record
ord-7af7b0f810a14263859bff3a32970b92
Source dataset
uspto-grants-1987_04
Patent number
US04656298

Reaction notes

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