Trifluoroacetic acid → 6-(2-Chloroethyl)-2H-benzo[b][1,4]oxazin-3(4H)-one

HRID 1435865Notes

Reaction equation

HRID 1435865 reaction equation
[Cl:1][CH2:2][C:3]([C:5]1[CH:6]=[CH:7][C:8]2[O:13][CH2:12][C:11](=[O:14])[NH:10][C:9]=2[CH:15]=1)=O.FC(F)(F)C(O)=O.C([SiH](CC)CC)C>CCOC(C)=O>[Cl:1][CH2:2][CH2:3][C:5]1[CH:6]=[CH:7][C:8]2[O:13][CH2:12][C:11](=[O:14])[NH:10][C:9]=2[CH:15]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 27644586-(2-chloroacetyl)-3,4-dihydro-2H-1,4-benzoxazin-3-one

Product 1

HCID 179831346-(2-Chloroethyl)-2H-benzo[b][1,4]oxazin-3(4H)-oneYield 95.8%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
45 °C

Procedure

To a dried flask under N2 atmosphere equipped with addition funnel was added 6-(2-chloroethanoyl)-4H-benzo[1,4]oxazin-3-one (10.0 g, 44.4 mmol) in trifluoroacetic acid (34 mL, 0.44 mol). To the resulting mixture at 0° C. was added triethylsilane (15.3 mL, 0.1 mole) dropwise over 5 min. The resulting mixture was warmed to 45° C. for 30 min and stirred at room temperature for 40 h. Reaction was poured onto ice water and layered with EtOAc. The organic layer was washed with water, brine, and dried over MgSO4. Solvent was removed on vacuum to give the desired compound as white solid (9.0 g, 93%). LC-MS (ES): m/e 212 (M+H)+.

Workup

  1. customTo a dried flask under N2 atmosphere equipped with addition funnel
  2. customReaction
  3. additionwas poured onto ice water
  4. washThe organic layer was washed with water, brine
  5. dry with materialdried over MgSO4
  6. customSolvent was removed on vacuum

Sources & evidence

ORD record
ord-5c5f542d1cb34216a47e8ea4b0fc5335
Source dataset
uspto-grants-2009_11
Patent number
US07618959B2

Reaction notes

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