Ammonium Chloride → 2-(5-Chloro-2-nitro-phenylamino)-5-methyl-thiophene-3-carbonitrile

HRID 131306

反応式

HRID 131306 の反応式
[NH2:1][C:2]1[S:3][C:4]([CH3:9])=[CH:5][C:6]=1[C:7]#[N:8].F[C:11]1[CH:16]=[C:15]([Cl:17])[CH:14]=[CH:13][C:12]=1[N+:18]([O-:20])=[O:19].O.[OH-].[Li+].[NH4+].[Cl-]>CS(C)=O>[Cl:17][C:15]1[CH:14]=[CH:13][C:12]([N+:18]([O-:20])=[O:19])=[C:11]([NH:1][C:2]2[S:3][C:4]([CH3:9])=[CH:5][C:6]=2[C:7]#[N:8])[CH:16]=1

参加物

6

反応物 4

HCID 25517Ammonium ChlorideHCID 696914-Chloro-2-fluoro-1-nitrobenzeneHCID 168937Lithium hydroxide, monohydrateHCID 6890562-Amino-5-methyl-3-thiophenecarbonitrile

生成物 1

HCID 586260242-(5-Chloro-2-nitro-phenylamino)-5-methyl-thiophene-3-carbonitrile収率 35%

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

実験手順

Dissolve 2-amino-5-methyl-thiophene-3-carbonitrile (0.79 g, 5.7 mmol) and 2-fluoro-4-chloronitrobenzene (1 g, 5.7 mmol) in dimethylsulfoxide (15 ml) and stir under nitrogen. Add lithium hydroxide monohydrate (250 mg, 6 mmol) and heat the mixture in an oil bath at 60° C. overnight. Pour the mixture into sat. NH4Cl(aq), extract into ethyl acetate, dry (MgSO4) and concentrate under reduced pressure. Chromatography on silica gel (eluent cyclohexane/ethylacetate) gives 2-(5-chloro-2-nitro-phenylamino)-5-methyl-thiophene-3-carbonitrile as a yellow solid (0.58 g, 35%): NMR (1H, 300 MHz, CDCl3): δ 9.6 (1H broad), 8.21 (1H,d), 7.09 (1H, s), 6.92 (1H,d), 6.80 (1H, s), 2.49 (3H,s).

後処理

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

出典と根拠

ORDレコード
ord-b5626db3a0cc401384b79ada74129211
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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