4-(Trifluoromethyl)benzamide → HCID 10566040, compound

HRID 2300598Notes

Reaction equation

HRID 2300598 reaction equation
[F:1][C:2]([F:13])([F:12])[C:3]1[CH:11]=[CH:10][C:6]([C:7]([NH2:9])=[O:8])=[CH:5][CH:4]=1.Br[CH:15]([CH3:23])[C:16](=O)[CH2:17][C:18]([O:20][CH3:21])=[O:19]>C1(C)C=CC=CC=1.O1CCOCC1>[CH3:21][O:20][C:18](=[O:19])[CH2:17][C:16]1[N:9]=[C:7]([C:6]2[CH:10]=[CH:11][C:3]([C:2]([F:12])([F:13])[F:1])=[CH:4][CH:5]=2)[O:8][C:15]=1[CH3:23]

Participants

5

Reactant 2

HCID 746844-(Trifluoromethyl)benzamideHCID 9815681Methyl 4-bromo-3-oxopentanoate

Product 1

HCID 10566040HCID 10566040, compoundYield 2.3%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 312751,4-DioxaneSolvent

Procedure

A mixture of 3.62 g (19.1 mmol) of 4-trifluoromethylbenzamide and 4.0 g (19 mmol) of methyl 4-bromo-3-oxo-pentanoate in 15 mL of toluene and 10 mL of dioxane (with 2 mL of EtOH) was refluxed for 22 h. The solution was concentrated under reduced pressure. The residue was taken into EtOAc and washed with water, brine, and dried over MgSO4. The crude material was purified by silica gel chromatography (10%-40% EtOAc in hexanes) to yield 130 mg of a yellow solid: 1H NMR (CDCl3, 400 MHz) δ8.1 (d, 2H, J=8.3), 7.65 (d, 2H, J=8.4), 3.75 (s, 3H), 3.58 (s, 2H), 2.39 (s, 3H); low resolution MS (ES+) m/e 300.0 (MH+).

Workup

  1. temperaturewas refluxed for 22 h
  2. concentrationThe solution was concentrated under reduced pressure
  3. washwashed with water, brine
  4. dry with materialdried over MgSO4
  5. customThe crude material was purified by silica gel chromatography (10%-40% EtOAc in hexanes)

Sources & evidence

ORD record
ord-988dcccb45834eeb9dc7226ce2e670a8
Source dataset
uspto-grants-2002_12
Patent number
US06498174B1

Reaction notes

Loading…