Pivaloyl chloride → HCID 178429852、化合物

HRID 1260362ノート

反応式

HRID 1260362 の反応式
[CH2:1]=[C:2]1[S:6][C:5](=[NH:7])[N:4]([C:8]2[CH:21]=[CH:20][C:11]3[O:12][C:13]([F:19])([F:18])[C:14]([F:17])([F:16])[O:15][C:10]=3[CH:9]=2)[CH2:3]1.CCN(C(C)C)C(C)C.[C:31](Cl)(=[O:36])[C:32]([CH3:35])([CH3:34])[CH3:33]>C(#N)C.C(Cl)Cl>[CH3:33][C:32]([CH3:35])([CH3:34])[C:31](/[N:7]=[C:5]1\[S:6][C:2]([CH3:1])=[CH:3][N:4]\1[C:8]1[CH:21]=[CH:20][C:11]2[O:12][C:13]([F:19])([F:18])[C:14]([F:16])([F:17])[O:15][C:10]=2[CH:9]=1)=[O:36]

参加物

6

反応物 3

HCID 62493Pivaloyl chloride2 回HCID 81531DiisopropylethylamineHCID 866191675-Methylene-3-(2,2,3,3-tetrafluoro-2,3-dihydrobenzo[b][1,4]dioxin-6-yl)thiazolidin-2-imine

生成物 1

HCID 178429852HCID 178429852、化合物

試薬・触媒・溶媒 2

HCID 6342Acetonitrile溶媒HCID 6344Dichloromethane溶媒

反応条件

温度
65 °C

実験手順

To a solution of 5-methylene-3-(2,2,3,3-tetrafluoro-2,3-dihydrobenzo[b][1,4]dioxin-6-yl)thiazolidin-2-imine (Example 22C, 0.14 g, 0.44 mmol) in acetonitrile (3 mL) was added Hunig's base (0.062 g, 0.48 mmol) followed by pivaloyl chloride (0.064 g, 0.54 mmol). The mixture was heated for 12 hours at 65° C. The mixture was cooled down and more pivaloyl chloride (0.064 g, 0.54 mmol) was added. The mixture was heated again at 65° C. for 12 hours. After cooling, the reaction mixture was diluted with CH2Cl2 (50 mL) and washed with water and brine. The organic phase was dried over sodium sulfate, filtered and dried. After evaporation under reduced pressure, the residue was chromatographed over silica using CH2Cl2-5% MeOH/CH2Cl2 to supply the titled compound. 1H NMR (CDCl3) δ ppm 1.05 (9 H), 2.30 (3 H), 6.80 (1 H), 7.20 (1 H), 7.40 (1 H), 7.50 (1 H); MS (ESI) m/z 405(M+H)+.

後処理

  1. temperatureThe mixture was cooled down
  2. temperatureThe mixture was heated again at 65° C. for 12 hours
  3. temperatureAfter cooling
  4. washwashed with water and brine
  5. dry with materialThe organic phase was dried over sodium sulfate
  6. filtrationfiltered
  7. customdried
  8. customAfter evaporation under reduced pressure
  9. customthe residue was chromatographed over silica

出典と根拠

ORDレコード
ord-4ffb4775997d4971b6dbff855604e540
出典データセット
uspto-grants-2013_06
特許番号
US08470813B2

反応ノート

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