Trifluoroacetic acid → 6-Amino-4-methyl-1,3-benzoxazol-2(3H)-one

HRID 1846427Notes

Reaction equation

HRID 1846427 reaction equation
C(O)(C(F)(F)F)=O.[CH3:8][C:9]1[C:14]2[NH:15][C:16](=[O:18])[O:17][C:13]=2[CH:12]=[C:11]([NH:19]C(=O)OC(C)(C)C)[CH:10]=1>C(Cl)Cl>[NH2:19][C:11]1[CH:10]=[C:9]([CH3:8])[C:14]2[NH:15][C:16](=[O:18])[O:17][C:13]=2[CH:12]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67126852Tert-butyl (4-methyl-2-oxo-2,3-dihydro-benzoxazol-6-yl)-carbamate

Product 1

HCID 199116046-Amino-4-methyl-1,3-benzoxazol-2(3H)-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

400 μL (5.30 mmol) TFA were added to 230 mg (0.900 mmol) tert-butyl (4-methyl-2-oxo-2,3-dihydro-benzoxazol-6-yl)-carbamate in 5.0 ml DCM and the mixture was stirred for 1.5 h at RT. The reaction mixture was evaporated down and the residue was divided between semisaturated sodium hydrogen carbonate solution and EtOAc. The organic phase was dried on sodium sulphate, filtered and evaporated down.

Workup

  1. customThe reaction mixture was evaporated down
  2. customThe organic phase was dried on sodium sulphate
  3. filtrationfiltered
  4. customevaporated down

Sources & evidence

ORD record
ord-baf8ec1fae1d465cbd77798864253e97
Source dataset
uspto-grants-2015_02
Patent number
US08952014B2

Reaction notes

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