4-(Trifluoromethoxy)aniline → 3-(3,4-Dichlorophenyl)-N-[4-(trifluoromethoxy)phenyl]prop-2-enamide

HRID 1283491Notes

Reaction equation

HRID 1283491 reaction equation
[F:1][C:2]([O:5][C:6]1[CH:11]=[CH:10][C:9]([NH2:12])=[CH:8][CH:7]=1)([F:4])[F:3].[Cl:13][C:14]1[CH:15]=[C:16]([CH:22]=[CH:23][C:24]=1[Cl:25])[CH:17]=[CH:18][C:19](Cl)=[O:20]>O1CCOCC1>[Cl:13][C:14]1[CH:15]=[C:16]([CH:22]=[CH:23][C:24]=1[Cl:25])[CH:17]=[CH:18][C:19]([NH:12][C:9]1[CH:10]=[CH:11][C:6]([O:5][C:2]([F:3])([F:4])[F:1])=[CH:7][CH:8]=1)=[O:20]

Participants

4

Reactant 2

HCID 6008484-(Trifluoromethoxy)anilineHCID 53411289HCID 53411289, compound

Product 1

HCID 539724313-(3,4-Dichlorophenyl)-N-[4-(trifluoromethoxy)phenyl]prop-2-enamide

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

p-Aminophenyl trifluoromethyl ether (0.7 g) pyridine (30 ml) and 3,4-dichlorocinnamoyl chloride (1 g) in dioxane (5 ml) were agitated and heated 3 hours at 80°-90° in a suitable flask fitted with a reflux condenser. The reaction mixture was then poured into 2 l. of ice-water containing conc. hydrochloric acid (50 ml). The crude product was filtered, washed with water and dried. It was recrystallized first from a blend of toluene (50 ml) and hexane (60 ml) and then from toluene (16 ml) and hexane (60 ml).

Workup

  1. temperatureheated 3 hours at 80°-90° in a suitable flask
  2. customfitted with a reflux condenser
  3. additionThe reaction mixture was then poured into 2 l
  4. filtrationThe crude product was filtered
  5. washwashed with water
  6. customdried
  7. customIt was recrystallized first from a blend of toluene (50 ml) and hexane (60 ml)

Sources & evidence

ORD record
ord-23c97ae571864631babfe1875acdd417
Source dataset
uspto-grants-1976_08
Patent number
US03975435

Reaction notes

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