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

HRID 131308

Reaktionsgleichung

Reaktionsgleichung von HRID 131308
[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

Komponenten

6

Edukt 4

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-086e4767ef7d4d3ca57bc77654685a55
Quelldatensatz
uspto-grants-2008_06
Patentnummer
US07384934B2

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