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

HRID 1435865노트

반응식

HRID 1435865 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

반응 조건

온도
45 °C

실험 절차

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)+.

후처리

  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

출처 및 근거

ORD 기록
ord-5c5f542d1cb34216a47e8ea4b0fc5335
출처 데이터셋
uspto-grants-2009_11
특허 번호
US07618959B2

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