Trifluoroacetic anhydride → 5-(N-benzylmethylamino)-4-methyl-2-phenyloxazole

HRID 26492Notes

Reaction equation

HRID 26492 reaction equation
[C:1]([NH:9][CH:10]([CH3:22])[C:11]([N:13]([CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)C)=[O:12])(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.F[C:24](F)(F)C(OC(=O)C(F)(F)F)=O.C(=O)([O-])[O-].[Na+].[Na+]>C(Cl)(Cl)Cl>[CH2:16]([CH2:15][NH:13][C:11]1[O:12][C:1]([C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[N:9][C:10]=1[CH3:22])[C:21]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:24]=1

Participants

5

Reactant 3

HCID 9845Trifluoroacetic anhydrideHCID 10340Sodium CarbonateHCID 213236262-Benzamido-N-benzyl-N-methylpropanamide

Product 1

HCID 213236355-(N-benzylmethylamino)-4-methyl-2-phenyloxazoleYield 82.8%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

2-Benzamido-N-benzyl-N-methylpropanamide (8.0 g., 0.0269 mol.), was dissolved in dry chloroform (40 ml.) and trifluoroacetic anhydride (17.0 g., 0.0809 mol.) was added dropwise with stirring under nitrogen. The mixture was stirred for 4 hours, then sufficient anhydrous sodium carbonate was added portionwise to neutralise the acid formed. The solid was filtered off and washed with dry chloroform (2× 10 ml.). The combined filtrates were evaporated under reduced pressure to give a brown oil, which was extracted with warm pentane. The pentane solution was evaporated to give a yellow oil 6.20 g. (82.5% IR and NMR confirm the structure.

Workup

  1. stirringThe mixture was stirred for 4 hours
  2. customformed
  3. filtrationThe solid was filtered off
  4. washwashed with dry chloroform (2× 10 ml.)
  5. customThe combined filtrates were evaporated under reduced pressure
  6. customto give a brown oil, which
  7. extractionwas extracted with warm pentane
  8. customThe pentane solution was evaporated

Sources & evidence

ORD record
ord-2bb484fe08ba41d3b6760dcd31368688
Source dataset
uspto-grants-1979_04
Patent number
US04150143

Reaction notes

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