Potassium Carbonate → 1-(Cyclopropanesulfonimidoyl)-4-nitrobenzene

HRID 1169712

反応式

HRID 1169712 の反応式
[CH:1]1([S:4]([C:6]2[CH:11]=[CH:10][C:9]([N+:12]([O-:14])=[O:13])=[CH:8][CH:7]=2)=[O:5])[CH2:3][CH2:2]1.FC(F)(F)C([NH2:19])=O.C(O)(=O)C.C(O)(=O)C.IC1C=CC=CC=1.[O-2].[Mg+2].C(=O)([O-])[O-].[K+].[K+]>ClCCl.CO.CC([O-])=O.CC([O-])=O.CC([O-])=O.CC([O-])=O.[Rh+2].[Rh+2].O>[N+:12]([C:9]1[CH:10]=[CH:11][C:6]([S:4]([CH:1]2[CH2:3][CH2:2]2)(=[NH:19])=[O:5])=[CH:7][CH:8]=1)([O-:14])=[O:13]

参加物

10

反応物 5

HCID 11430Potassium CarbonateHCID 67717TrifluoroacetamideHCID 6850729Magnesium monoxideHCID 12217721Iodo benzene diacetateHCID 595508341-(Cyclopropanesulfinyl)-4-nitrobenzene

生成物 1

HCID 569492531-(Cyclopropanesulfonimidoyl)-4-nitrobenzene

試薬・触媒・溶媒 4

HCID 152122Dirhodium tetraacetate触媒HCID 887Methanol溶媒HCID 962Water溶媒HCID 6344Dichloromethane溶媒

実験手順

6.6 g (31.24 mmol) (RS)-1-(cyclopropylsulphinyl)-4-nitrobenzene, 7.77 g (68.74 mmol) trifluoroacetamide, 16.6 g (51.55 mmol) iodobenzene diacetate and 5.54 g (137.5 mmol) magnesium oxide are placed in 350 ml dichloromethane. The mixture is stirred for 5 minutes, treated with 0.69 g (1.56 mmol) rhodium(II) acetate dimer and stirred at room temperature for 12 hours. The suspension is diluted with 235 ml methanol, treated with 23.75 g potassium carbonate and stirred at room temperature for 4 hours. Next the mixture is treated with 400 ml water, and the organic phase is separated and filtered at the pump through Celite®. The aqueous phase is extracted several times with dichloromethane. The combined organic phases are washed with half-saturated sodium chloride solution and stirred with 100 ml 2N hydrochloric acid for 30 minutes. The aqueous phase is adjusted to pH 9 with concentrated sodium hydroxide solution with ice cooling. The crystallised product is aspirated dry, washed with water and dried. 4.7 g (66.5% of theor.) of the product is obtained.

後処理

  1. stirringstirred at room temperature for 12 hours
  2. stirringstirred at room temperature for 4 hours
  3. customthe organic phase is separated
  4. filtrationfiltered at the pump through Celite®
  5. extractionThe aqueous phase is extracted several times with dichloromethane
  6. washThe combined organic phases are washed with half-saturated sodium chloride solution
  7. stirringstirred with 100 ml 2N hydrochloric acid for 30 minutes
  8. washwashed with water
  9. customdried
  10. custom4.7 g (66.5% of theor.) of the product is obtained

出典と根拠

ORDレコード
ord-2a1117d856ea4c8798f9b9626365bf9b
出典データセット
uspto-grants-2010_11
特許番号
US07825128B2

関連ノート

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