Ammonia → N2-methyl-5-trifluoromethylsulfanylpyridine-2,3-diamine

HRID 923813노트

반응식

HRID 923813 반응식
Br[C:2]1[C:3]([NH:13][CH3:14])=[N:4][CH:5]=[C:6]([S:8][C:9]([F:12])([F:11])[F:10])[CH:7]=1.C(CC(=O)C)(=O)C.C(=O)([O-])[O-].[Cs+].[Cs+].[NH3:28]>[Cu+2].C(CC(=O)C)(=O)C.O.CN1C(=O)CCC1>[CH3:14][NH:13][C:3]1[C:2]([NH2:28])=[CH:7][C:6]([S:8][C:9]([F:12])([F:11])[F:10])=[CH:5][N:4]=1

참가 물질

8

반응물 4

HCID 222AmmoniaHCID 10796Cesium carbonateHCID 31261AcetylacetoneHCID 67981267(3-Bromo-5-trifluoromethylsulfanylpyridine-2-yl)-methylamine

생성물 1

HCID 68091243N2-methyl-5-trifluoromethylsulfanylpyridine-2,3-diamine

시약·촉매·용매 3

HCID 21863952acetylacetone copper(II)촉매HCID 962Water용매HCID 13387N-methyl-2-pyrrolidone용매

반응 조건

온도
110 °C

실험 절차

To a pressure-resistant reaction container, (3-bromo-5-trifluoromethylsulfanylpyridine-2-yl)-methylamine (1.96 g), acetylacetone copper (II) (89 mg), acetylacetone (0.27 g), cesium carbonate (2.34 g), and NMP (7 ml), 28% of aqueous ammonia (5 ml) was added, and stirred at 110° C. for 8.5 hours. After the mixture was cooled to room temperature, into the reaction mixture, water was poured. The insoluble material was filtered through Celite®, and then the filtered material was washed with ethyl acetate, and filtrate was extracted with ethyl acetate. The combined organic layer was dried over sodium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography to give 1.18 g of N2-methyl-5-trifluoromethylsulfanylpyridine-2,3-diamine (Compound (1F)-3).

후처리

  1. additionwas poured
  2. filtrationThe insoluble material was filtered through Celite®
  3. washthe filtered material was washed with ethyl acetate, and filtrate
  4. extractionwas extracted with ethyl acetate
  5. dry with materialThe combined organic layer was dried over sodium sulfate
  6. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-1148cf024f344b1bbfdc27ff41b5b930
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09278983B2

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