N-(4-fluoro-phenyl)-N-pyridin-2-ylmethyl-6-chloro-nicotinamide → Thionicotinamide

HRID 404760

反応式

HRID 404760 の反応式
FC1C=CC([N:8](CC2C=CC=CN=2)[C:9](=O)[C:10]2[CH:15]=[CH:14][C:13](Cl)=[N:12][CH:11]=2)=CC=1.[SH2:25].[Na]>CN(C)C=O.C(OCC)(=O)C>[C:9]([NH2:8])(=[S:25])[C:10]1[CH:15]=[CH:14][CH:13]=[N:12][CH:11]=1

参加物

5

反応物 2

HCID 59446415N-(4-fluoro-phenyl)-N-pyridin-2-ylmethyl-6-chloro-nicotinamideHCID 86586439Sodium hydrogen sulphide

生成物 1

HCID 737155Thionicotinamide収率 82%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

In a round bottom flask, N-(4-fluoro-phenyl)-N-pyridin-2-ylmethyl-6-chloro-nicotinamide intermediate X (1.078 g, 3.16 mmol) and anhydrous sodium hydrogen sulfide (0.354 g, 6.32 mmol) was suspended in anhydrous dimethylformamide (10 mL). The suspension was heated to reflux, and the reaction mixture turned a deep green color. After 1 h, the reaction mixture was diluted with ethyl acetate (50 mL) and washed with water (20 mL). The aqueous layer was back extracted with ethyl acetate (2×20 ml), and the organic layers combined and washed with saturated aqueous sodium chloride, dried over sodium sulfate, filtered and evaporated by rotary evaporation to yield 0.88 g (82%) of thionicotinamide intermediate XI as a dark yellow oil. TLC (EtOAc/hexanes, 2:1) Rf=0.1; ESI-MS m/z=339.9 [M+H]+.

後処理

  1. temperatureThe suspension was heated
  2. temperatureto reflux
  3. washwashed with water (20 mL)
  4. extractionThe aqueous layer was back extracted with ethyl acetate (2×20 ml)
  5. washwashed with saturated aqueous sodium chloride
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. customevaporated by rotary evaporation

出典と根拠

ORDレコード
ord-afd7bf82aaee4c1693024db9f017b9ce
出典データセット
uspto-grants-2014_06
特許番号
US08748623B2

関連ノート

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