Triphenylphosphine → Benzenesulfonamide

HRID 4739

반응식

HRID 4739 반응식
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

참가 물질

8

반응물 3

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

생성물 1

HCID 7370Benzenesulfonamide

시약·촉매·용매 4

HCID 24290Palladium Chloride촉매HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 6228Dimethylformamide용매HCID 8471Triethylamine용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-9ef1ffbbe2ba4e948cd69ef247efc7ac
출처 데이터셋
uspto-grants-1988_02
특허 번호
US04727186

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