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

HRID 1192082

Reaction equation

[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]

Participants

Conditions

Temperature: 100 °C

Procedure

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]+.

Workup

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

Sources & evidence

ORD record: ord-31fe241f358849b38de6d3b4dd6f088e
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08680139B2

Linked notes

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