Water → HCID 54293928, compound

HRID 1979797Notes

Reaction equation

HRID 1979797 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=O.[NH2:10][CH2:11][P:12](=[O:19])([O:16][CH2:17][CH3:18])[O:13][CH2:14][CH3:15].C1(C)C=CC=CC=1.O>C(OCC)(=O)C>[Cl:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[N:10][CH2:11][P:12](=[O:19])([O:16][CH2:17][CH3:18])[O:13][CH2:14][CH3:15]

Participants

6

Reactant 4

HCID 962WaterHCID 1140TolueneHCID 69962-ChlorobenzaldehydeHCID 1596920Diethyl (aminomethyl)phosphonate

Product 1

HCID 54293928HCID 54293928, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

14 g. (0.1 mol) 2-chlorobenzaldehyde are added dropwise, at ambient temperature, to a solution of 16.7 g. (0.1 mol) diethyl aminomethylphosphonate in 200 ml. toluene. When the addition has ended, stirring is continued for 30 minutes. The water formed during the reaction is removed by decantation. The toluene phase is washed with 50 ml. of a saturated aqueous solution of sodium chloride, dried over anhydrous sodium sulphate and then evaporated. This gives 29 g. (yield: 100%) diethyl N-(o-chlorobenzylidene)-aminomethylphosphonate in the form of a yellow oil giving a single spot in TLC (silica plate, eluant: ethyl acetate, Rf=0.45).

Workup

  1. additionWhen the addition
  2. customis removed by decantation
  3. washThe toluene phase is washed with 50 ml
  4. dry with materialof a saturated aqueous solution of sodium chloride, dried over anhydrous sodium sulphate
  5. customevaporated

Sources & evidence

ORD record
ord-862878fe8af84be6b0c7d3f0594712d0
Source dataset
uspto-grants-1984_11
Patent number
US04482718

Reaction notes

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