Isovaleryl chloride → HCID 178429853、化合物

HRID 1260364ノート

反応式

HRID 1260364 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][CH:32]([CH3:37])[CH2:33][C:34](Cl)=[O:35]>C(#N)C.C(Cl)Cl>[CH3:31][CH:32]([CH3:37])[CH2:33][C:34](/[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:35]

参加物

6

反応物 3

HCID 66054Isovaleryl 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 178429853HCID 178429853、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-methylbutanoyl chloride (0.08 g, 0.66 mmol). The mixture was heated for 12 hours at 65° C. The reaction mixture was cooled down and more 3-methylbutanoyl chloride (0.08 g, 0.66 mmol) was added. The mixture was heated again at 65° C. for 12 hours. After cooling off, the 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 100%-5% MeOH/CH2Cl2 to supply the titled compound. 1H NMR (CDCl3) δ ppm 0.95 (6 H), 2.20 (1 H), 2.35 (3 H), 2.40 (2 H), 6.75 (1 H), 7.20 (1 H), 7.30 (1 H), 7.40 (1 H); MS (ESI) m/z 405(M+H)+.

後処理

  1. temperatureThe reaction mixture was cooled down
  2. temperatureThe mixture was heated again at 65° C. for 12 hours
  3. temperatureAfter cooling off
  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 the residue
  9. customwas chromatographed over silica

出典と根拠

ORDレコード
ord-a3fca7cec24a46d49cb581bc552bca84
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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