Hydrochloric Acid → 2-(4-Chloro-2-nitro-phenylamino)-5-methyl-thiophene-3-carbonitrile

HRID 131308

反応式

HRID 131308 の反応式
[NH2:1][C:2]1[S:3][C:4]([CH3:9])=[CH:5][C:6]=1[C:7]#[N:8].Cl[C:11]1[CH:16]=[C:15](Cl)[CH:14]=[CH:13][C:12]=1[N+:18]([O-:20])=[O:19].O.[OH-].[Li+].[ClH:24]>CS(C)=O>[Cl:24][C:16]1[CH:15]=[CH:14][C:13]([NH:1][C:2]2[S:3][C:4]([CH3:9])=[CH:5][C:6]=2[C:7]#[N:8])=[C:12]([N+:18]([O-:20])=[O:19])[CH:11]=1

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 118992,4-DichloronitrobenzeneHCID 168937Lithium hydroxide, monohydrateHCID 6890562-Amino-5-methyl-3-thiophenecarbonitrile

生成物 1

HCID 586259752-(4-Chloro-2-nitro-phenylamino)-5-methyl-thiophene-3-carbonitrile収率 33%

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

実験手順

Dissolve 2-amino-5-methyl-thiophene-3-carbonitrile (4.14 g, 30 mmol) and 2,4-dichloronitrobenzene (5.76 g, 30 mmol) in dimethylsulfoxide (70 ml) and stir under nitrogen. Add lithium hydroxide monohydrate (2.0 g, 47.7 mmol) and heat the mixture in an oil bath at room temperature for 18 hours. Pour the mixture into ice water, make acid with 2N HCl, extract into ethyl acetate, dry (MgSO4) and concentrate under reduced pressure. Crystallize from ethanol to give 2-(4-chloro-2-nitro-phenylamino)-5-methyl-thiophene-3-carbonitrile as a yellow solid (2.92 g, 33%): NMR (1H, 300 MHz, CDCl3): δ 9.5 (1H broad), 8.25 (1H,s), 7.45 (1H, d), 7.1 (1H,d), 6.25 (1H, s), 2.5 (3H,s).

後処理

  1. extractionextract into ethyl acetate
  2. dry with materialdry (MgSO4)
  3. concentrationconcentrate under reduced pressure
  4. customCrystallize from ethanol

出典と根拠

ORDレコード
ord-086e4767ef7d4d3ca57bc77654685a55
出典データセット
uspto-grants-2008_06
特許番号
US07384934B2

関連ノート

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