Trifluoroacetic acid → 7-(Trifluoroacetylamino)-2,3-dihydrobenzofuran

HRID 1940591Notes

Reaction equation

HRID 1940591 reaction equation
[O:1]1[C:5]2[C:6](C(O)=O)=[CH:7][CH:8]=[CH:9][C:4]=2[CH2:3][CH2:2]1.[N-:13]=[N+]=[N-].[Na+].[F:17][C:18]([F:23])([F:22])[C:19](O)=[O:20]>FC(F)(F)C(OC(=O)C(F)(F)F)=O>[F:17][C:18]([F:23])([F:22])[C:19]([NH:13][C:6]1[C:5]2[O:1][CH2:2][CH2:3][C:4]=2[CH:9]=[CH:8][CH:7]=1)=[O:20]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 33557Sodium AzideHCID 27950142,3-Dihydro-1-benzofuran-7-carboxylic acid

Product 1

HCID 214634927-(Trifluoroacetylamino)-2,3-dihydrobenzofuranYield 82%

Reagents, catalysts & solvents 1

HCID 9845Trifluoroacetic anhydrideSolvent

Procedure

2,3-dihydrobenzofuran-7-carboxylic acid (D1) (1.42 g) was dissolved in a mixture of trifluoroacetic acid (50 ml) and trifluoroacetic anhydride (10 ml). After stirring at room temperature for 1.5 h, the mixture was cooled to 0° C. and treated portionwise with sodium azide (788 mg, 1.4 eq.), then stirred at room temperature for 2 days under argon. The mixture was evaporated under reduced pressure, and the residue partitioned between CHCl3 and water. The organic phase was washed with K2CO3 (aq), dried (Na2SO4) and the solvent evaporated under reduced pressure, to give the title compound (1.64 g, 82%) as an off-white crystalline material.

Workup

  1. temperaturethe mixture was cooled to 0° C.
  2. stirringstirred at room temperature for 2 days under argon
  3. customThe mixture was evaporated under reduced pressure
  4. customthe residue partitioned between CHCl3 and water
  5. washThe organic phase was washed with K2CO3 (aq)
  6. dry with materialdried (Na2SO4)
  7. customthe solvent evaporated under reduced pressure

Sources & evidence

ORD record
ord-fc15626c49e14c6fafd41690553010e0
Source dataset
uspto-grants-1997_12
Patent number
US05700818

Reaction notes

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