Sodium hydride → HCID 178490687、化合物

HRID 78536

反応式

HRID 78536 の反応式
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:17][CH3:18])=[C:6]([CH:16]=1)[C:7]([NH:9][C:10]1[S:11][C:12]([CH3:15])=[CH:13][N:14]=1)=[O:8].[H-].[Na+].Cl[CH2:22][C:23]1[O:24][CH:25]=[CH:26][CH:27]=1>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:17][CH3:18])=[C:6]([CH:16]=1)[C:7](/[N:9]=[C:10]1\[S:11][C:12]([CH3:15])=[CH:13][N:14]\1[CH2:22][C:23]1[O:24][CH:25]=[CH:26][CH:27]=1)=[O:8]

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 2195202-(Chloromethyl)furanHCID 26781445-chloro-2-methoxy-N-(5-methyl-1,3-thiazol-2-yl)benzamide

生成物 1

HCID 178490687HCID 178490687、化合物収率 39%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a solution of Example 340A (0.15 g, 0.53 mmol) in 5 mL DMF was added sodium hydride (0.016 g, 0.67 mmol, 95%). After the solution was allowed to stir at ambient temperature for 30 min, 2-(chloromethyl)furan (0.08 g, 0.67 mmol) was added. The reaction was held at ambient temperature overnight and then quenched with water. The crude was extracted with ethyl acetate and the organics washed with water, then dried over MgSO4, filtered, and concentrated. Flash chromatography over silica gel (50% ethyl acetate/hexane) gave 0.075 g of the title compound. 1H NMR (300 MHz, DMSO-d6) δ ppm 2.26 (d, J=1.36 Hz, 3H) 3.80 (s, 3H) 5.18 (s, 2H) 6.54 (s, 1H) 7.12 (d, J=8.81 Hz, 1H) 7.29 (d, J=1.36 Hz, 1H) 7.46 (dd, J=8.81, 2.71 Hz, 1H) 7.64 (t, J=1.70 Hz, 1H) 7.67-7.76 (m, 2H). m/z 363.0 (M+H)+.

後処理

  1. waitThe reaction was held at ambient temperature overnight
  2. customquenched with water
  3. extractionThe crude was extracted with ethyl acetate
  4. washthe organics washed with water
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated

出典と根拠

ORDレコード
ord-f5d5b07db2fc404bae3845a0aa036456
出典データセット
uspto-grants-2014_09
特許番号
US08841334B2

関連ノート

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