Potassium Carbonate → HCID 22347996、化合物

HRID 897261ノート

反応式

HRID 897261 の反応式
C([N:5]1[C:14](=[O:15])[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([Cl:16])[CH:12]=2)[NH:7][C:6]1=[O:17])(C)(C)C.O([CH2:26][C:27]([F:30])([F:29])[F:28])S(C(F)(F)F)(=O)=O.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[Cl:16][C:11]1[CH:12]=[C:13]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:26][C:27]([F:30])([F:29])[F:28])[C:6](=[O:17])[NH:5][C:14]2=[O:15]

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 803662,2,2-Trifluoroethyl trifluoromethanesulfonateHCID 223480083-tert-Butyl-6-chloro-1H-quinazoline-2,4-dione

生成物 1

HCID 22347996HCID 22347996、化合物収率 99.4%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

反応条件

温度
50 °C

実験手順

To a solution of 3-tert-butyl-6-chloro-1H-quinazoline-2,4-dione (1.0 g, 3.97 mmol) in acetonitrile (40 mL) was added trifluoroethyl triflate (0.736 mL, 4.76 mmol) and potassium carbonate (821 mg, 5.95 mmol). The reaction was heated to 50° C. and stirred 48 hrs. The solution was cooled, concentrated, and dissolved in ethyl acetate. The solution was washed with sodium bicarbonate, brine, dried over Na2SO4, filtered, and concentrated. The crude residue was dissolved in acetic acid and treated with 4 mL HBr solution (30 weight % in AcOH). The reaction was stirred for 3 hours at room temperature, and concentrated to provide 1.1 g of yellow solid. 1H NMR (300 MHz, CD3OD) δ ppm 4.96 (q, J=8.7 Hz, 2H), 7.53 (d, J=9.0 Hz, 1H), 7.75 (dd, J=2.6, 9.1 Hz, 1H), 8.07 (d, J=2.7 Hz, 1H); MS (ESI+Q1MS) m/z 279 [M+H]+

後処理

  1. temperatureThe solution was cooled
  2. concentrationconcentrated
  3. dissolutiondissolved in ethyl acetate
  4. washThe solution was washed with sodium bicarbonate, brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. dissolutionThe crude residue was dissolved in acetic acid
  9. additiontreated with 4 mL HBr solution (30 weight % in AcOH)
  10. stirringThe reaction was stirred for 3 hours at room temperature
  11. concentrationconcentrated

出典と根拠

ORDレコード
ord-cf5fbb5c24904e6ab321bf7f83105e4e
出典データセット
uspto-grants-2005_07
特許番号
US06921821B2

反応ノート

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