Sulfuric Acid → 5-((3,5-Dichloropyridin-4-yl)thio)-4-nitrothiophene-2-carboxylic acid

HRID 1192082

Reaktionsgleichung

Reaktionsgleichung von HRID 1192082
[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Cl:22])[C:7]=1[S:8][C:9]1[S:13][C:12]([C:14]([O:16]CC)=[O:15])=[CH:11][C:10]=1[N+:19]([O-:21])=[O:20].S(=O)(=O)(O)O>O>[Cl:22][C:6]1[CH:5]=[N:4][CH:3]=[C:2]([Cl:1])[C:7]=1[S:8][C:9]1[S:13][C:12]([C:14]([OH:16])=[O:15])=[CH:11][C:10]=1[N+:19]([O-:21])=[O:20]

Komponenten

4

Edukt 2

HCID 1118Sulfuric AcidHCID 60207318Ethyl 5-[(3,5-dichloro-4-pyridyl)sulfanyl]-4-nitro-thiophene-2-carboxylate

Produkt 1

HCID 602073175-((3,5-Dichloropyridin-4-yl)thio)-4-nitrothiophene-2-carboxylic acidAusbeute 78,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

Ethyl 5-[(3,5-dichloro-4-pyridyl)sulfanyl]-4-nitro-thiophene-2-carboxylate (1.8 g, 4.74 mmol) was added to a solution of concentrated sulfuric acid (10 mL) diluted with water (20 mL), and the resulting mixture was heated at 100° C. for 5 hours. After this time, the mixture was poured into ice (4.5 mL) and stirred at room temperature for 20 minutes, then the resulting solid was collected by filtration, washed with water and dried in vacuo at 40° C. overnight to afford the title product as a white solid (1.3 g, 78% yield). 1H NMR (400 MHz, d6-DMSO) δ: 9.0 (2H, s), 8.1 (1H, s). MS m/z: 350.85, 352.90 [M+H]+.

Aufarbeitung

  1. filtrationthe resulting solid was collected by filtration
  2. washwashed with water
  3. customdried in vacuo at 40° C. overnight

Quellen und Nachweise

ORD-Eintrag
ord-31fe241f358849b38de6d3b4dd6f088e
Quelldatensatz
uspto-grants-2014_03
Patentnummer
US08680139B2

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