Acetonitrile → 2-(4-(Methoxymethoxy)phenoxy)-N-(4-(trifluoromethoxy)phenyl)propanamide

HRID 1655553Notes

Reaction equation

HRID 1655553 reaction equation
Br[CH:2]([CH3:17])[C:3]([NH:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][C:13]([F:16])([F:15])[F:14])=[CH:8][CH:7]=1)=[O:4].[CH3:18][O:19][CH2:20][O:21][C:22]1[CH:27]=[CH:26][C:25]([OH:28])=[CH:24][CH:23]=1.C(=O)([O-])[O-].[K+].[K+].C(#N)C>O>[CH3:18][O:19][CH2:20][O:21][C:22]1[CH:27]=[CH:26][C:25]([O:28][CH:2]([CH3:17])[C:3]([NH:5][C:6]2[CH:11]=[CH:10][C:9]([O:12][C:13]([F:16])([F:15])[F:14])=[CH:8][CH:7]=2)=[O:4])=[CH:24][CH:23]=1

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 11430Potassium CarbonateHCID 150701674-(Methoxymethoxy)phenolHCID 197926812-bromo-N-(4-(trifluoromethoxy)phenyl)propanamide

Product 1

HCID 197926762-(4-(Methoxymethoxy)phenoxy)-N-(4-(trifluoromethoxy)phenyl)propanamide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 2.91 g (9.3 mmol) of 2-bromo-N-(4-(trifluoromethoxy)phenyl)propanamide, 1.58 g (10 mmol) of 4-(methoxymethoxy)phenol, 1.52 g (11 mmol) of powdered, anhydrous potassium carbonate and 35 ml of acetonitrile was warmed, under N2, at reflux for a period of 5.5 hours and then stirred at room temperature overnight. The resulting mixture was poured into water and extracted with two portions of ether. The combined organic layers were washed twice with 5 percent aqueous NaOH, treated with charcoal and MgSO4, filtered and the filtrates evaporated to dryness. The residue was recrystallized from hexane to leave 1.77 g (49 percent of theoretical) of the above-named product as a colorless solid, m.p. 115°-116° C. The product is identified on the basis of IR and NMR analyses.

Workup

  1. temperatureat reflux for a period of 5.5 hours
  2. extractionextracted with two portions of ether
  3. washThe combined organic layers were washed twice with 5 percent aqueous NaOH
  4. additiontreated with charcoal and MgSO4
  5. filtrationfiltered
  6. customthe filtrates evaporated to dryness
  7. customThe residue was recrystallized from hexane

Sources & evidence

ORD record
ord-c5f7eccc7ea4492a8deec7465b0cf9ab
Source dataset
uspto-grants-1993_10
Patent number
US05250690

Reaction notes

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