Pyridine → 2-bromo-N-(4-(trifluoromethoxy)phenyl)propanamide

HRID 1655552Notes

Reaction equation

HRID 1655552 reaction equation
[Br:1][CH:2]([CH3:6])[C:3](Cl)=[O:4].Cl.[F:8][C:9]([F:19])([F:18])[O:10][C:11]1[CH:17]=[CH:16][C:14]([NH2:15])=[CH:13][CH:12]=1.N1C=CC=CC=1>C(Cl)Cl>[Br:1][CH:2]([CH3:6])[C:3]([NH:15][C:14]1[CH:16]=[CH:17][C:11]([O:10][C:9]([F:8])([F:18])[F:19])=[CH:12][CH:13]=1)=[O:4]

Participants

5

Reactant 3

HCID 1049PyridineHCID 979802-Bromopropanoyl chlorideHCID 27810604-(trifluoromethoxy)aniline Hydrochloride

Product 1

HCID 197926812-bromo-N-(4-(trifluoromethoxy)phenyl)propanamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 4.02 g (23.4 mmol) of 2-bromopropionyl chloride in 10 ml of methylene chloride was added to an ice-cooled solution of 5.0 g (23.4 mmol) of 4-(trifluoromethoxy)aniline hydrochloride, 4.65 g (59 mmol) of pyridine and 30 ml of methylene chloride. The mixture was stirred at ambient temperature for a period of 2.5 hours and then washed with two portions of dilute aqueous HCl and two portions of saturated aqueous sodium bicarbonate, dried over MgSO4, treated with charcoal, filtered and the filtrates evaporated to dryness. The residue was recrystallized from methylcyclohexane to give 5.43 g 74 percent of theoretical) of the above-named product as colorless crystals, m.p. 111°-112° C.

Workup

  1. washwashed with two portions of dilute aqueous HCl and two portions of saturated aqueous sodium bicarbonate
  2. dry with materialdried over MgSO4
  3. additiontreated with charcoal
  4. filtrationfiltered
  5. customthe filtrates evaporated to dryness
  6. customThe residue was recrystallized from methylcyclohexane

Sources & evidence

ORD record
ord-dd9c798f3f424ef982fb3206e63b003d
Source dataset
uspto-grants-1993_10
Patent number
US05250690

Reaction notes

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