Triethylamine → 3-[4-[(6-Bromohexyl)oxy]but-1-ynyl}benzenesulfonamide

HRID 720845

反応式

HRID 720845 の反応式
Br[C:2]1[CH:3]=[C:4]([S:8]([NH2:11])(=[O:10])=[O:9])[CH:5]=[CH:6][CH:7]=1.[CH2:12]([O:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][Br:23])[CH2:13][C:14]#[CH:15].C(N(CC)CC)C>O1CCCC1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl.[Cu]I.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[Br:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][O:16][CH2:12][CH2:13][C:14]#[C:15][C:2]1[CH:3]=[C:4]([S:8]([NH2:11])(=[O:10])=[O:9])[CH:5]=[CH:6][CH:7]=1

参加物

8

反応物 3

HCID 8471TriethylamineHCID 27347653-Bromobenzene-1-sulfonamideHCID 113792816-Bromohexylbut-3-ynyl ether

生成物 1

HCID 218955583-[4-[(6-Bromohexyl)oxy]but-1-ynyl}benzenesulfonamide収率 90.7%

試薬・触媒・溶媒 4

HCID 11776Triphenylphosphine触媒HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 6102075Dichlorobis(triphenylphosphine)palladium触媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
50 °C

実験手順

A mixture of 3-bromo-benzenesulfonamide (625 g), 6-bromohexyl but-3-ynyl ether (850.1 g), bis(triphenylphosphine)palladium (II) chloride (62.5 g), triphenylphosphine (18.1 g) and triethylamine (536.3 g) in tetrahydrofuran (6250 ml) was stirred under an atmosphere of nitrogen for 20 mins. Copper (I) iodide (12.5 g) was then added to give a dark red/brown mixture that was heated to 50° C. for 23 h. The reaction mixture was then cooled to room temperature and filtered through a short silica pad (1000 g). The pad was washed with additional tetrahydrofuran (15.6 L) and the resulting solution then concentrated under reduced pressure to give crude product (1382 g) as a viscous oil. This was purified by chromatography (7 kg silica) eluting with 5:1 petroleum ether:ethyl acetate followed by 2:1 petroleum ether:ethyl acetate to give the title compound (932.9 g) as an oil, LC RT=5.69 min, δ (DMSO-d6) 7.79 (1H, s), 7.76 (1H, d, J 7.6 Hz), 7.56 (2H, m), 7.42 (2H, m), 3.55 (2H, t, J 6.6 Hz), 3.49 (2H, t, J 6.6 Hz), 3.42 (2H, t, J 6.6 Hz), 2.68 (2H, t, J 6.6 Hz), 1.76 (2H, m), 1.50 (2H, m), 1.35 (4H, m).

後処理

  1. customto give a dark red/brown mixture that
  2. temperatureThe reaction mixture was then cooled to room temperature
  3. filtrationfiltered through a short silica pad (1000 g)
  4. washThe pad was washed with additional tetrahydrofuran (15.6 L)
  5. concentrationthe resulting solution then concentrated under reduced pressure
  6. customto give crude product (1382 g) as a viscous oil
  7. customThis was purified by chromatography (7 kg silica)
  8. washeluting with 5:1 petroleum ether

出典と根拠

ORDレコード
ord-89789490575441eb9773dc2d93502ab3
出典データセット
uspto-grants-2006_11
特許番号
US07135600B2

関連ノート

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