Tosylmethyl isocyanide → 3-(3,4-Dichlorophenyl)-4-nitro-1H-pyrrole

HRID 1085614ノート

反応式

HRID 1085614 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][C:12]=1[Cl:13])[CH:5]=[CH:6][N+:7]([O-:9])=[O:8].C1(C)C=CC(S([CH2:23][N+:24]#[C-:25])(=O)=O)=CC=1>CS(C)=O.CCOCC.O>[Cl:1][C:2]1[CH:3]=[C:4]([C:5]2[C:6]([N+:7]([O-:9])=[O:8])=[CH:25][NH:24][CH:23]=2)[CH:10]=[CH:11][C:12]=1[Cl:13]

参加物

6

反応物 2

HCID 161915Tosylmethyl isocyanideHCID 2362903,4-Dichloro-beta-nitrostyrene

生成物 1

HCID 4704323-(3,4-Dichlorophenyl)-4-nitro-1H-pyrrole収率 212.2%

試薬・触媒・溶媒 3

HCID 679Dimethyl Sulfoxide溶媒HCID 962Water溶媒HCID 3283Diethyl Ether溶媒2 回

実験手順

Sodium hydride (2.66 g of a 60% suspension in oil is rinsed with dry ether; 66 mmol) and suspended in 150 mL of dry ether. To this mixture is added over 15 minutes a mixture of 12.0 g (5.5 mmol) of 3,4-dichloro-β-nitrostyrene and 10.8 g (5.5 mmol) of (p-tolylsulfonyl)methyl isocyanide in 50 mL of DMSO and 150 mL of ether. The mixture is stirred for 1.5 hours and then diluted with 150-200 mL of water and additional ether. The ether layer is separated, dried over magnesium sulfate, and concentrated in vacuo. The resulting 10.6 g of crude product is purified by chromatography on silica gel using a 4:1 mixture of chloroform and ethyl acetate. A 7.2 g solid fraction is recrystallized from chloroform-ethyl acetate-hexane to give 3.0 g of yellow solid, m.p. 187°-188° C. (dec.).

後処理

  1. washSodium hydride (2.66 g of a 60% suspension in oil is rinsed with dry ether
  2. additionTo this mixture is added over 15 minutes
  3. customThe ether layer is separated
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe resulting 10.6 g of crude product is purified by chromatography on silica gel using
  7. additiona 4:1 mixture of chloroform and ethyl acetate
  8. customA 7.2 g solid fraction is recrystallized from chloroform-ethyl acetate-hexane

出典と根拠

ORDレコード
ord-71e325f0ba254ea08a3033e61ca4ec91
出典データセット
uspto-grants-1991_04
特許番号
US05010098

反応ノート

読み込み中…