Triethylamine → (E)-2-(4-chloro-phenyl)-ethenesulfonic acid (1,1,3,3-tetramethyl-butyl)-amide

HRID 1272354ノート

反応式

HRID 1272354 の反応式
[CH3:1][C:2]([NH:9][S:10]([CH:13]=[CH2:14])(=[O:12])=[O:11])([CH3:8])[CH2:3][C:4]([CH3:7])([CH3:6])[CH3:5].[Cl:15][C:16]1[CH:21]=[CH:20][C:19](OC)=[C:18](I)[CH:17]=1.C(N(CC)CC)C>CN(C)C=O.ClCCl.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH3:8][C:2]([NH:9][S:10](/[CH:13]=[CH:14]/[C:19]1[CH:20]=[CH:21][C:16]([Cl:15])=[CH:17][CH:18]=1)(=[O:12])=[O:11])([CH3:1])[CH2:3][C:4]([CH3:5])([CH3:6])[CH3:7]

参加物

8

反応物 3

HCID 8471TriethylamineHCID 28009784-Chloro-2-iodoanisoleHCID 17748074N-(2,4,4-Trimethylpentan-2-yl)ethenesulfonamide

生成物 1

HCID 17748075(E)-2-(4-chloro-phenyl)-ethenesulfonic acid (1,1,3,3-tetramethyl-butyl)-amide収率 46%

試薬・触媒・溶媒 4

HCID 11776Triphenylphosphine触媒HCID 167845palladium(II) acetate触媒HCID 6228Dimethylformamide溶媒HCID 6344Dichloromethane溶媒

反応条件

温度
140 °C

実験手順

Ethenesulfonic acid (1,1,3,3-tetramethyl-butyl)-amide (8.5 g, 38.8 mmol) and 4-chloroiodoanisole (7.87 g, 33.0 mmol) was dissolved in N,N-dimethylformamide (65 ml). Palladium acetate (139 mg, 0.62 mmol) and triphenylphosphine (357 mg, 1.36 mmol) was added to the reaction followed by triethylamine (12.5 ml, 89.3 mmol). The reaction was flushed with nitrogen and heated at 140° C. for 16 hours. The reaction was cooled to room temperature and quenched with 1N HCl (250 ml). The aqueous solution was extracted with ethyl acetate (3×200 ml). The organic solution was dried over MgSO4, filtered and concentrated in vacuo to afford a solid. The solid was dissolved in dichloromethane and purified by dry flash chromatography (SiO2, heptane to 1:1 heptane: ethyl acetate). The fractions were combined to afford (E)-2-(4-chloro-phenyl)-ethenesulfonic acid (1,1,3,3-tetramethyl-butyl)-amide (5.0 g, 46% yield).

後処理

  1. customThe reaction was flushed with nitrogen
  2. temperatureThe reaction was cooled to room temperature
  3. customquenched with 1N HCl (250 ml)
  4. extractionThe aqueous solution was extracted with ethyl acetate (3×200 ml)
  5. dry with materialThe organic solution was dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customto afford a solid
  9. custompurified
  10. dry with materialby dry flash chromatography (SiO2, heptane to 1:1 heptane: ethyl acetate)

出典と根拠

ORDレコード
ord-d44128a8f7034191b481ad78c66e2f04
出典データセット
uspto-grants-2007_04
特許番号
US07208526B2

反応ノート

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