Thionyl Chloride → 3-Chlorothiophene-2-carbonyl chloride

HRID 566204

Reaktionsgleichung

Reaktionsgleichung von HRID 566204
S(Cl)([Cl:3])=O.[Cl:5][C:6]1[CH:10]=[CH:9][S:8][C:7]=1[C:11]([OH:13])=O>C1(C)C=CC=CC=1>[Cl:5][C:6]1[CH:10]=[CH:9][S:8][C:7]=1[C:11]([Cl:3])=[O:13]

Komponenten

4

Edukt 2

HCID 24386Thionyl ChlorideHCID 7012693-Chlorothiophene-2-carboxylic acid

Produkt 1

HCID 27358243-Chlorothiophene-2-carbonyl chloride

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

Excess thionyl chloride (3.5 ml, 48.0 mmoles) was added to 0.85 g (5.2 mmoles) of 3-Chloro-2-thiophenecarboxylic acid (prepared according to Corral, C., et al., Heterocycles 23:1431 (1985)) dissolved in 50 ml of toluene and stirring at room temperature. After addition the solution was refluxed for 3 hours to form 3-chloro-2-thiophenecarbonyl chloride. Concentration of the reaction solution gave the acid chloride as a white solid. The acid chloride was then dissolved in 4 ml of N,N-dimethylformamide and slowly added to a cooled (ice/water bath) stirring solution of 5-chloro-2-oxindole-1-carboxamide (1.0 g, 4.71 mmoles) and 4-(N,N-dimethylamino)pyridine (1.3 g, 10.5 mmoles) in 10 ml of N,N-dimethylformamide. After 45 minutes the solution was allowed to warm to room temperature and after 2 hours was worked-up by pouring into a mixed ice/6 N hydrochloric acid solution. A yellow precipitate formed. The precipitate was filtered, washed with water and dried to give 1.3 g of impure product as a yellow solid. Recrystallization with acetic acid/heptane (2:1) gave 0.77 g (2.2 mmoles) of pure title compound as yellow needles, m.p. 222-224° C. Total yield of product was 42%.

Aufarbeitung

  1. additionAfter addition the solution
  2. temperaturewas refluxed for 3 hours

Quellen und Nachweise

ORD-Eintrag
ord-6ccdf940967f4b09ba9e11a915397c3f
Quelldatensatz
uspto-grants-2001_01
Patentnummer
US06174883B1

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