(Aminomethyl)phosphonic acid → HCID 22132222, compound

HRID 618645Notes

Reaction equation

HRID 618645 reaction equation
[NH2:1][CH2:2][P:3]([OH:6])(=[O:5])[OH:4].[F:7][C:8]([F:21])([F:20])[C:9]1[CH:10]=[C:11]([N+:17]([O-:19])=[O:18])[C:12](Cl)=[CH:13][C:14]=1[Cl:15]>O.C(O)C>[N+:17]([C:11]1[CH:10]=[C:9]([C:8]([F:7])([F:20])[F:21])[C:14]([Cl:15])=[CH:13][C:12]=1[NH:1][CH2:2][P:3]([OH:6])(=[O:4])[OH:5])([O-:19])=[O:18]

Participants

5

Reactant 2

HCID 14017(Aminomethyl)phosphonic acidHCID 6211792,4-Dichloro-5-nitrobenzotrifluoride

Product 1

HCID 22132222HCID 22132222, compoundYield 68.2%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
120 °C

Procedure

3.3 g (30 mmol) of aminomethanephosphonic acid in 120 ml of water and 120 ml of ethanol are introduced together with 3.37 g (31.8 mmol) of soda and mixed with 7.8 g (97%, 30 mmol) of 3-trifluoromethyl-4,6-dichloronitrobenzene, and it is refluxed for 4 hours at 120° C. bath temperature. After removing the ethanol in a rotary evaporator, it is extracted three times with 100 ml of ethyl acetate. The organic phase is washed with a little water. It contains starting material and is discarded. The collected aqueous phase is adjusted acidic with 4 N hydrochloric acid to pH 1 and extracted three times with 100 ml of ethyl acetate each. The organic phase is washed with water, dried, filtered and concentrated by evaporation. 6.85 g (68% of theory) of N-(2-nitro-4-trifluoromethyl-5-chloro-phenyl)-aminomethanephosphonic acid of melting point 207.3° C. is obtained.

Workup

  1. customAfter removing the ethanol
  2. customin a rotary evaporator, it
  3. extractionis extracted three times with 100 ml of ethyl acetate
  4. washThe organic phase is washed with a little water
  5. extractionextracted three times with 100 ml of ethyl acetate each
  6. washThe organic phase is washed with water
  7. customdried
  8. filtrationfiltered
  9. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-59297c84265743d68a9221d0db48b81b
Source dataset
uspto-grants-1999_09
Patent number
US05955461

Reaction notes

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