Acetic Acid → 3-(3,5-Dichloro-benzylamino)propyl(diethoxymethyl)phosphinic acid ethyl ester

HRID 1440679Notes

Reaction equation

HRID 1440679 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([Cl:10])[CH:9]=1)[CH:5]=O.[CH2:11]([O:13][P:14]([CH2:23][CH2:24][CH2:25][NH2:26])([CH:16]([O:20][CH2:21][CH3:22])[O:17][CH2:18][CH3:19])=[O:15])[CH3:12].C(O)(=O)C.C([BH3-])#N.[Na+]>CO>[CH2:11]([O:13][P:14]([CH2:23][CH2:24][CH2:25][NH:26][CH2:5][C:4]1[CH:3]=[C:2]([Cl:1])[CH:9]=[C:8]([Cl:10])[CH:7]=1)([CH:16]([O:20][CH2:21][CH3:22])[O:17][CH2:18][CH3:19])=[O:15])[CH3:12]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 357463,5-DichlorobenzaldehydeHCID 5003444Sodium cyanoborohydrideHCID 10422382Phosphinic acid, (3-aminopropyl)(diethoxymethyl)-, ethyl ester

Product 1

HCID 218053273-(3,5-Dichloro-benzylamino)propyl(diethoxymethyl)phosphinic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

1.41 g of 3,5-dichlorobenzaldehyde are added to a solution of 2.53 g of 3-aminopropyl(diethoxymethyl)phosphinic acid ethyl ester in 10 ml of anhydrous methanol and the resulting clear solution is stirred at room temperature for 30 minutes. There are then added first 0.6 g of glacial acetic acid and then, dropwise, 0.21 g of sodium cyanoborohydride dissolved in 5 ml of methanol. An exothermic reaction begins. The reaction mixture is stirred for 3 hours at 20°, adjusted to pH 8, and the solvent is removed. The residue is dissolved in dichloromethane and washed with water. The organic phase is separated off, dried over sodium sulfate and concentrated to dryness by evaporation. The oil that remains behind is purified by chromatography on silica gel, yielding 3-(3,5-dichloro-benzylamino)propyl(diethoxymethyl)phosphinic acid ethyl ester in the form of a yellowish oil.

Workup

  1. customAn exothermic reaction
  2. stirringThe reaction mixture is stirred for 3 hours at 20°
  3. customthe solvent is removed
  4. dissolutionThe residue is dissolved in dichloromethane
  5. washwashed with water
  6. customThe organic phase is separated off
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated to dryness by evaporation
  9. customThe oil that remains behind is purified by chromatography on silica gel

Sources & evidence

ORD record
ord-f5a11c96ee764f5d8068c202acbb25df
Source dataset
uspto-grants-1996_03
Patent number
US05500418

Reaction notes

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