Water → HCID 67096922, 화합물

HRID 404863노트

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HRID 404863 반응식
[CH:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][CH:6]=1)([CH3:3])[CH3:2].Br[C:13]1[S:14][CH:15]=[CH:16][N:17]=1.C(=O)([O-])[O-].[K+].[K+].O>CS(C)=O>[CH:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([O:11][C:13]2[S:14][CH:15]=[CH:16][N:17]=2)=[CH:7][CH:6]=1)([CH3:3])[CH3:2]

참가 물질

6

반응물 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 764302-BromothiazoleHCID 820014-Isopropoxyphenol

생성물 1

HCID 67096922HCID 67096922, 화합물수율 91.4%

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

실험 절차

A mixture of Example 1A (15.5 g, 0.1 mol), 2-bromothiazole (18.2 g, 0.11 mol) and potassium carbonate (15.2 g, 0.11 mol) in dimethylsulfoxide was heated at 160° C. under nitrogen for six hours. After cooling and treating with water, the aqueous phase was extracted with dichloromethane. The organic layer was washed with brine, dried, and concentrated to give 27.5 g of the crude as a dark brown oil, which was purified on a silica gel (ethyl acetate/hexane 5-35%) to afford 21.5 g of the product as a brown oil (91% yield) 1H NMR (500 MHz, CDCl3) δ ppm 1.32-1.36 (m, 6H) 1.34 (none, 6H) 1.34 (none, 5 H) 4.45-4.57 (m, 1H) 6.76 (d, J=3.91 Hz, 1H) 6.87-6.93 (m, 2H) 7.15-7.20 (m, 2H) 7.21 (d, J=3.91 Hz, 1H). MS (ESI): m/z 236 (M+H).

후처리

  1. temperatureAfter cooling
  2. extractionthe aqueous phase was extracted with dichloromethane
  3. washThe organic layer was washed with brine
  4. customdried
  5. concentrationconcentrated
  6. customto give 27.5 g of the crude as a dark brown oil, which
  7. customwas purified on a silica gel (ethyl acetate/hexane 5-35%)

출처 및 근거

ORD 기록
ord-41af5234463e4d3aacf4624e236ccc55
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08748627B2

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