Water → HCID 67096922、化合物

HRID 404863

反応式

HRID 404863 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

HCID 67096922HCID 67096922、化合物収率 91.4%

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

実験手順

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).

後処理

  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%)

出典と根拠

ORDレコード
ord-41af5234463e4d3aacf4624e236ccc55
出典データセット
uspto-grants-2014_06
特許番号
US08748627B2

関連ノート

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