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

HRID 923813ノート

反応式

HRID 923813 の反応式
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

参加物

8

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 21863952acetylacetone copper(II)触媒HCID 962Water溶媒HCID 13387N-methyl-2-pyrrolidone溶媒

反応条件

温度
110 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-1148cf024f344b1bbfdc27ff41b5b930
出典データセット
uspto-grants-2016_03
特許番号
US09278983B2

反応ノート

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