Dimethyl Sulfoxide → HCID 11516373、化合物

HRID 1987224

反応式

HRID 1987224 の反応式
F[C:2]1[CH:7]=[CH:6][C:5]([NH:8][S:9]([CH2:12][CH3:13])(=[O:11])=[O:10])=[CH:4][C:3]=1[N+:14]([O-:16])=[O:15].[F:17][C:18]1([F:26])[CH2:23][CH2:22][CH:21]([CH2:24][NH2:25])[CH2:20][CH2:19]1.CS(C)=O.C(CN)O>O>[F:17][C:18]1([F:26])[CH2:23][CH2:22][CH:21]([CH2:24][NH:25][C:2]2[CH:7]=[CH:6][C:5]([NH:8][S:9]([CH2:12][CH3:13])(=[O:11])=[O:10])=[CH:4][C:3]=2[N+:14]([O-:16])=[O:15])[CH2:20][CH2:19]1

参加物

6

反応物 4

HCID 679Dimethyl SulfoxideHCID 700EthanolamineHCID 3286362N-(4-fluoro-3-nitrophenyl)ethanesulfonamide2 回HCID 156044941-(4,4-Difluorocyclohexyl)methanamine

生成物 1

HCID 11516373HCID 11516373、化合物収率 63.8%

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
65 °C

実験手順

N-(4-Fluoro-3-nitrophenyl)ethanesulfonamide (26 g, 0.107 mol), [(4,4-difluorocyclohexyl)methyl]amine (approx. 15 g), DIPFA (20 mL) and DMSO (100 mL) were mixed together and heated to 65° C. overnight. Ethanolamine (5 g) was added and the reaction mixture was stirred until complete disappearance of N-(4-fluoro-3-nitrophenyl)ethanesulfonamide (approx. 4-5 hrs.). The room temperature cooled down reaction mixture was poured in cold water (900 mL). The product was extracted with DCM (5×200 mL). The combined organic phases were washed with HCl 2N (3×200 mL) and dried over anhydrous Na2SO4. The solvent was removed and the crude product was purified on silica gel by flash chromatography (this material can be re-crystallized using a mixture of EtOAc and hexane) to provide the title product (24.2 g) as orange solid.

後処理

  1. temperatureThe room temperature cooled down
  2. customreaction mixture
  3. extractionThe product was extracted with DCM (5×200 mL)
  4. washThe combined organic phases were washed with HCl 2N (3×200 mL)
  5. dry with materialdried over anhydrous Na2SO4
  6. customThe solvent was removed
  7. customthe crude product was purified on silica gel by flash chromatography (this material
  8. customcan be re-crystallized
  9. additiona mixture of EtOAc and hexane)

出典と根拠

ORDレコード
ord-98c8825b80c04d309453a53714842663
出典データセット
uspto-grants-2009_06
特許番号
US07550495B2

関連ノート

読み込み中…