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

HRID 1750053ノート

反応式

HRID 1750053 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

1.96 g of (3-bromo-5-trifluoromethylsulfanylpyridin-2-yl)-methylamine, 89 mg of acetylacetone copper(II), 0.27 g of acetylacetone, 2.34 g of cesium carbonate, 7 ml of NMP and 5 ml of aqueous ammonia (28%) were charged to a pressure-resistant reactor and stirred at 110° C. for 8.5 hours. Water was added to the reaction mixture cooled to room temperature, and the insoluble matter was filtered with celite (registered trademark), and then the filtered matter was washed with ethyl acetate, and the filtrate was extracted with ethyl acetate. The combined organic layer was dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The resulting residue was applied to a silica gel column chromatography to obtain 1.18 g of N2-methyl-5-trifluoromethylsulfanylpyridine-2,3-diamine.

後処理

  1. temperaturecooled to room temperature
  2. filtrationthe insoluble matter was filtered with celite (registered trademark)
  3. washthe filtered matter was washed with ethyl acetate
  4. extractionthe filtrate was extracted with ethyl acetate
  5. dry with materialThe combined organic layer was dried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-0348384267e94c4f870e3c1b538a9756
出典データセット
uspto-grants-2015_10
特許番号
US09156838B2

反応ノート

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