Dimethylformamide → 2-(5-Methoxy-pent-1-yn-1-yl)-benzenesulfonamide

HRID 6379

反応式

HRID 6379 の反応式
CN(C)C=O.I[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[S:13]([NH2:16])(=[O:15])=[O:14].[CH2:17]([O:22][CH3:23])[CH2:18][CH2:19][C:20]#[CH:21]>[Cu]I.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C(N(CC)CC)C>[CH3:23][O:22][CH2:17][CH2:18][CH2:19][C:20]#[C:21][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[S:13]([NH2:16])(=[O:15])=[O:14]

参加物

7

反応物 3

HCID 6228DimethylformamideHCID 28248922-Iodobenzene-1-sulfonamideHCID 142211075-Methoxypent-1-yne

生成物 1

HCID 197936262-(5-Methoxy-pent-1-yn-1-yl)-benzenesulfonamide

試薬・触媒・溶媒 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 178418476HCID 178418476、化合物触媒HCID 8471Triethylamine溶媒

実験手順

135 ml of N,N-dimethylformamide and 22 ml of triethylamine are taken and 7.5 g of 2-iodobenzenesulfonamide, 2.6 g of pent-4-yn-1-yl-methyl ether as well as 0.067 g of copper(I) iodide and 0.144 g of bis(triphenylphosphine)palladium(II) dichloride are added. The reaction mixture is heated to 65° and stirred for 22 hours at that temperature under argon. After that time, the N,N-dimethylformamide is distilled off at 0.1 torr and 40°. The crude product is purified on 500 g of silica gel (Merck Si 60, 40-63 μm) with hexane/ethyl acetate=2/1 as eluant. The fractions containing the product are concentrated by evaporation at 15 torr and 40° to yield white crystalline 2-(5-methoxy-pent-1-yn-1-yl)-benzenesulfonamide, melting point: 59°-61°.

後処理

  1. temperatureThe reaction mixture is heated to 65°
  2. distillationAfter that time, the N,N-dimethylformamide is distilled off at 0.1 torr and 40°
  3. customThe crude product is purified on 500 g of silica gel (Merck Si 60, 40-63 μm) with hexane/ethyl acetate=2/1 as eluant
  4. additionThe fractions containing the product
  5. concentrationare concentrated by evaporation at 15 torr and 40°

出典と根拠

ORDレコード
ord-f88643d947a34b82bf524f131968accd
出典データセット
uspto-grants-1993_09
特許番号
US05248693

関連ノート

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