2-Chloroaniline → 5-bromo-N-(2-chlorophenyl)thiophene-2-carboxamide

HRID 1524221

Reaktionsgleichung

Reaktionsgleichung von HRID 1524221
[Br:1][C:2]1[S:6][C:5]([C:7]([OH:9])=O)=[CH:4][CH:3]=1.C(Cl)(=O)C(Cl)=O.[Cl:16][C:17]1[CH:23]=[CH:22][CH:21]=[CH:20][C:18]=1[NH2:19].CCN(C(C)C)C(C)C.Cl.[Cl-].[Na+].O>C(Cl)Cl.CC(=O)OCC.CN(C=O)C>[Br:1][C:2]1[S:6][C:5]([C:7]([NH:19][C:18]2[CH:20]=[CH:21][CH:22]=[CH:23][C:17]=2[Cl:16])=[O:9])=[CH:4][CH:3]=1

Komponenten

9

Edukt 5

HCID 72402-ChloroanilineHCID 65578Oxalyl chlorideHCID 81531DiisopropylethylamineHCID 3491155-Bromothiophene-2-carboxylic acidHCID 131718760Hydrochloric acid brine

Produkt 1

HCID 35083965-bromo-N-(2-chlorophenyl)thiophene-2-carboxamideAusbeute 92 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 6228DimethylformamideLösungsmittelHCID 6344DichloromethaneLösungsmittel2×HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A mixture of 5-bromo-thiophene-2-carboxylic acid (5) (207 mg, 1 mmol), oxalyl chloride (420 μl) and catalytic amount of DMF in 5 ml DCM was stirred at r.t for 2 h before evaporation to dryness. The resulting solid residue was dissolved in 5 ml DCM and to which were added 2-chloroaniline (209 μl, 2 eq) and DIEA (522 μl). The reaction mixture was stirred at r.t for overnight before worked up with EA/aq. HCl/brine. The org. phase was concentrated and then purified on a flash silica gel column to give 291 mg (5-bromo(2-thienyl))-N-(2-chlorophenyl)carboxamide (7) as light yellow solid. (yield: 92%, purity>90%).

Aufarbeitung

  1. stirringThe reaction mixture was stirred at r.t for overnight
  2. concentrationphase was concentrated
  3. custompurified on a flash silica gel column

Quellen und Nachweise

ORD-Eintrag
ord-36e9c8c99c2d4d308436fb1f1de5d4ee
Quelldatensatz
uspto-grants-2015_07
Patentnummer
US09079891B2

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