Triphenylphosphine → Benzenesulfonamide

HRID 4739

反応式

HRID 4739 の反応式
I[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([NH2:11])(=[O:10])=[O:9].P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.CC(C(OC1C=CC(C(O)CNC)=CC=1OC(C(C)(C)C)=O)=O)(C)C.Cl>CN(C)C=O.C(N(CC)CC)C.Cl[Pd]Cl.[Cu]I>[C:3]1([S:8]([NH2:11])(=[O:10])=[O:9])[CH:4]=[CH:5][CH:6]=[CH:7][CH:2]=1

参加物

8

反応物 3

HCID 11776TriphenylphosphineHCID 71486Dipivefrin HydrochlorideHCID 28248922-Iodobenzene-1-sulfonamide

生成物 1

HCID 7370Benzenesulfonamide

試薬・触媒・溶媒 4

HCID 24290Palladium Chloride触媒HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 6228Dimethylformamide溶媒HCID 8471Triethylamine溶媒

実験手順

To a solution of 28.3 g (0.1 mole) of 2-iodophenylsulfonamide in 350 ml of dimethylformamide and 100 ml of triethylamine are added 1.0 g of palladium dichloro-bis(triphenylphosphite) complex, PdCl2 [P(C6H5)3 ]2, and 0.5 g of copper(I) iodide (CuI). Gaseous propine is then introduced into this solution until the starting material is completely reacted. The reaction mixture is filtered and the residue is concentrated in vacuo and then taken up in water. The precipitate is isolated and dried. Recrystallisation from ethyl acetate/hexane yields 15.6 g (80%) of 2-propyn-1-yl)phenylsulfonamide with a melting point of 147°-149° C.

後処理

  1. customis completely reacted
  2. filtrationThe reaction mixture is filtered
  3. concentrationthe residue is concentrated in vacuo
  4. customThe precipitate is isolated
  5. customdried
  6. customRecrystallisation from ethyl acetate/hexane

出典と根拠

ORDレコード
ord-9ef1ffbbe2ba4e948cd69ef247efc7ac
出典データセット
uspto-grants-1988_02
特許番号
US04727186

関連ノート

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