Isovaleryl chloride → HCID 178429853, 화합물

HRID 1260364노트

반응식

HRID 1260364 반응식
[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]

참가 물질

6

반응물 3

HCID 66054Isovaleryl chloride2회HCID 81531DiisopropylethylamineHCID 866191675-Methylene-3-(2,2,3,3-tetrafluoro-2,3-dihydrobenzo[b][1,4]dioxin-6-yl)thiazolidin-2-imine

생성물 1

HCID 178429853HCID 178429853, 화합물

시약·촉매·용매 2

HCID 6342Acetonitrile용매HCID 6344Dichloromethane용매

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온도
65 °C

실험 절차

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)+.

후처리

  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

출처 및 근거

ORD 기록
ord-a3fca7cec24a46d49cb581bc552bca84
출처 데이터셋
uspto-grants-2013_06
특허 번호
US08470813B2

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