Aniline → HCID 12906001, compound

HRID 1105730Notes

Reaction equation

HRID 1105730 reaction equation
[F:1][C:2]([F:23])([F:22])[C:3]1[CH:21]=[CH:20][C:6]([O:7][C:8]2[CH:19]=[CH:18][C:11]([O:12][CH:13]([CH3:17])[C:14](Cl)=[O:15])=[CH:10][CH:9]=2)=[CH:5][CH:4]=1.FC(F)(F)C1C=CC(OC2C=CC(OC(C)C(O)=O)=CC=2)=CC=1.S(Cl)(Cl)=O.[NH2:51][C:52]1[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=1>C1C=CC=CC=1.O>[F:1][C:2]([F:23])([F:22])[C:3]1[CH:21]=[CH:20][C:6]([O:7][C:8]2[CH:19]=[CH:18][C:11]([O:12][CH:13]([CH3:17])[C:14]([NH:51][C:52]3[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=3)=[O:15])=[CH:10][CH:9]=2)=[CH:5][CH:4]=1

Participants

7

Reactant 4

HCID 6115AnilineHCID 24386Thionyl ChlorideHCID 181206TrifopHCID 129060152-{4-[4-(Trifluoromethyl)phenoxy]phenoxy}propanoyl chloride

Product 1

HCID 12906001HCID 12906001, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 962WaterSolvent

Procedure

34.5 g of α-[4-(4-trifluoromethylphenoxy)phenoxy]propionyl chloride synthesized by a conventional method (as described in, for example, Synthetic Organic Chemistry, supra) from α-[4-(4-trifluoromethylphenoxy)phenoxy]propionic acid and thionyl chloride was dissolved in 200 ml of benzene, and while maintaining the solution at 20° to 25° C., 19.5 g of aniline was added. The reaction was performed at 30° C. for 1 hour. The reaction product was poured into 300 ml of water to precipitate and washed with water, and then dried with anhydrous sodium sulfate. After drying, benzene was evaporated off, and the residue was recrystallized from a mixture of ethanol and petroleum ether (2:1 by volume) to afford 36 g of the final product having a melting point of 129° to 131° C. The yield was 90%.

Workup

  1. temperaturewhile maintaining the solution at 20° to 25° C.
  2. customto precipitate
  3. washwashed with water
  4. dry with materialdried with anhydrous sodium sulfate
  5. customAfter drying
  6. custombenzene was evaporated off
  7. customthe residue was recrystallized from a mixture of ethanol and petroleum ether (2:1 by volume)

Sources & evidence

ORD record
ord-788e0cd5233b4629acfb26717f2fd240
Source dataset
uspto-grants-1982_01
Patent number
US04309562

Reaction notes

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