Potassium Carbonate → HCID 46932057, compound

HRID 1192044Notes

Reaction equation

Cl[C:2]1[S:6][C:5]([C:7](=[O:9])[CH3:8])=[CH:4][C:3]=1[N+:10]([O-:12])=[O:11].[Na].[Cl:14][C:15]1[CH:16]=[N+:17]([O-:23])[CH:18]=[C:19]([Cl:22])[C:20]=1[SH:21].C(=O)([O-])[O-].[K+].[K+]>>[Cl:14][C:15]1[CH:16]=[N+:17]([O-:23])[CH:18]=[C:19]([Cl:22])[C:20]=1[S:21][C:2]1[S:6][C:5]([C:7](=[O:9])[CH3:8])=[CH:4][C:3]=1[N+:10]([O-:12])=[O:11]

Participants

Reactant 3

HCID 11430Potassium Carbonate

HCID 5211051-(5-Chloro-4-nitrothiophen-2-yl)ethan-1-one

HCID 178507103HCID 178507103, compound

Product 1

HCID 46932057HCID 46932057, compoundYield 63%

Procedure

To a solution of 1-(5-Chloro-4-nitro-2-thienyl)ethanone (0.209 g, 1 mmol) in N,N-dimethylformide (4 mL), was added 3,5-dichloro-1-oxido-pyridin-1-ium-4-thiol sodium salt (0.2 g, 1 mmol) and potassium carbonate (0.348 g, 2.56 mmol). The resulting reaction mixture was stirred at ambient temperature for 4 hours. The reaction mixture was poured onto ice (5 mL). After stirring for 10 minutes the solid which formed was collected by filtration and washed with water (10 mL) and air dried. The crude solid product was purified by silica gel flash chromatography using a mixture of 90:10 dichloromethane and methanol as eluent to afford the title product as a yellow solid (0.23 g, 63% yield). 1H NMR (400 MHz, d6-DMSO) δ: 8.93 (1H, s) 8.54 (1H, s), 2.54 (3H, s). MS m/z: 363.0 [M+H]+.

Workup

customThe resulting reaction mixture
additionThe reaction mixture was poured onto ice (5 mL)
stirringAfter stirring for 10 minutes the solid which
customformed
filtrationwas collected by filtration
washwashed with water (10 mL) and air
customdried
customThe crude solid product was purified by silica gel flash chromatography
additiona mixture of 90:10 dichloromethane and methanol as eluent

Sources & evidence

ORD record: ord-e81f517d862a43b5b87ff2bfdb2d4b82
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08680139B2

Reaction notes

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