Water → HCID 54293928, compound

HRID 2412661Notes

Reaction equation

HRID 2412661 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>CCOC(C)=O>[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 to give 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: AcOEt, 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
  6. customto give 29 g

Sources & evidence

ORD record
ord-e6b3d4a86f1241229df096b81c5d8f91
Source dataset
uspto-grants-1985_01
Patent number
US04493931

Reaction notes

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