Water → N-(2-nitro-4-trifluoromethyl-5-chloro-phenyl)-aminomethanephosphonic acid
Reaction equation
[NH2:1][CH2:2][P:3]([OH:6])(=[O:5])[OH:4].O.[F:8][C:9]([F:22])([F:21])[C:10]1[CH:11]=[C:12]([N+:18]([O-:20])=[O:19])[C:13](Cl)=[CH:14][C:15]=1[Cl:16]>C(#N)C>[N+:18]([C:12]1[CH:11]=[C:10]([C:9]([F:8])([F:21])[F:22])[C:15]([Cl:16])=[CH:14][C:13]=1[NH:1][CH2:2][P:3]([OH:6])(=[O:4])[OH:5])([O-:20])=[O:19]Participants
Conditions
- Temperature
- 120 °C
Procedure
) 3.3 g (30 mmol) of aminomethanephosphonic acid is introduced into 120 ml of water and 120 ml of acetonitrile 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 refluxed for 4 hours at a bath temperature of 120° C. After the acetonitrile is drawn off 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 made acidic at pH 1 with 4N hydrochloric acid 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 with a melting point of 207.3° C. is obtained.
Workup
- customAfter the acetonitrile is drawn off in a rotary evaporator, it
- extractionis extracted three times with 100 ml of ethyl acetate
- washThe organic phase is washed with a little water
- extractionextracted three times with 100 ml of ethyl acetate each
- washThe organic phase is washed with water
- customdried
- filtrationfiltered
- concentrationconcentrated by evaporation
Sources & evidence
- ORD record
- ord-7e94b2c4f93e4fdb83fa452f7d78d6d8
- Source dataset
- uspto-grants-2000_11
- Patent number
- US06143733
Reaction notes
Loading…