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

HRID 1435865ノート

反応式

HRID 1435865 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

反応条件

温度
45 °C

実験手順

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)+.

後処理

  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

出典と根拠

ORDレコード
ord-5c5f542d1cb34216a47e8ea4b0fc5335
出典データセット
uspto-grants-2009_11
特許番号
US07618959B2

反応ノート

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