Phosphorus oxychloride → HCID 23085677, compound

HRID 2243099Notes

Reaction equation

HRID 2243099 reaction equation
[F:1][C:2]([F:13])([F:12])[C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][CH:11]=1)[C:6](Cl)=[O:7].O[C:15]1[CH:21]=[CH:20][C:19]([N+:22]([O-:24])=[O:23])=[CH:18][C:16]=1[NH2:17].O=P(Cl)(Cl)Cl>C1(C)C=CC=CC=1>[F:1][C:2]([F:13])([F:12])[C:3]1[CH:4]=[C:5]([C:6]2[O:7][C:15]3[CH:21]=[CH:20][C:19]([N+:22]([O-:24])=[O:23])=[CH:18][C:16]=3[N:17]=2)[CH:9]=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 752573-(Trifluoromethyl)benzoyl chlorideHCID 36133892-Amino-4-Nitrophenol

Product 1

HCID 23085677HCID 23085677, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

3-Trifluoromethylbenzoyl chloride (9.03 g, 0.043 mol) and 2-hydroxy-5-nitroaniline (6.58 g, 0.041 mol) in toluene (200 ml) are refluxed for 48 hours. POCl3 (20 ml) is added, the mixture is refluxed for a further 2 hours and concentrated, and the solid is recrystallized from NaOH (pH=10). The product is filtered off and recrystallized from water and finally from isopropyl ether. Yield: 10.3 g (78%); Rf (8/2 petroleum ether/ethyl acetate): 0.58; IR (KBr): 3085, 1620, 1531, 1425, 1340 cm−1.

Workup

  1. temperaturethe mixture is refluxed for a further 2 hours
  2. concentrationconcentrated
  3. customthe solid is recrystallized from NaOH (pH=10)
  4. filtrationThe product is filtered off
  5. customrecrystallized from water and finally from isopropyl ether

Sources & evidence

ORD record
ord-36a2cdba5385400a97a89045cc0b6815
Source dataset
uspto-grants-2010_03
Patent number
US07674809B2

Reaction notes

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