3,3-Dimethylbutanoyl chloride → HCID 178429851、化合物

HRID 1260363ノート

反応式

HRID 1260363 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.[CH3:31][C:32]([CH3:38])([CH3:37])[CH2:33][C:34](Cl)=[O:35]>C(#N)C.C(Cl)Cl>[CH3:31][C:32]([CH3:38])([CH3:37])[CH2:33][C:34](/[N:7]=[C:5]1\[S:6][C:2](=[CH2:1])[CH2:3][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:35]

参加物

6

反応物 3

HCID 815143,3-Dimethylbutanoyl chlorideHCID 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 178429851HCID 178429851、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 3,3-dimethylbutanoyl chloride (0.088 g, 0.66 mmol). The mixture was heated for 12 hours at 65° C. The reaction mixture was cooled down, 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 1.00 (9 H), 2.35 (2 H), 4.65 (2 H), 5.25 (1 H), 5.35 (1 H), 7.15 (1 H), 7.25 (1 H), 7.55 (1 H); MS (ESI) m/z 419(M+H)+.

後処理

  1. temperatureThe reaction mixture was cooled down
  2. washwashed with water and brine
  3. dry with materialThe organic phase was dried over sodium sulfate
  4. filtrationfiltered
  5. customdried
  6. customAfter evaporation under reduced pressure
  7. customthe residue was chromatographed over silica

出典と根拠

ORDレコード
ord-d8612ba2949945878f8513182fc6e3cc
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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