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

HRID 131308

반응식

HRID 131308 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-086e4767ef7d4d3ca57bc77654685a55
출처 데이터셋
uspto-grants-2008_06
특허 번호
US07384934B2

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