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

HRID 404760

반응식

HRID 404760 반응식
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

참가 물질

5

반응물 2

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

생성물 1

HCID 737155Thionicotinamide수율 82%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

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]+.

후처리

  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

출처 및 근거

ORD 기록
ord-afd7bf82aaee4c1693024db9f017b9ce
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08748623B2

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