Sodium Hydroxide → 5-((3,5-Dichloropyridin-4-yl)thio)-4-nitrothiophene-2-carboxylic acid

HRID 1192075

Reaction equation

HRID 1192075 reaction equation
[OH-].[Na+].[Cl:3][C:4]1[CH:5]=[N:6][CH:7]=[C:8]([Cl:23])[C:9]=1[S:10][C:11]1[S:15][C:14]([C:16]([O:18]C)=[O:17])=[CH:13][C:12]=1[N+:20]([O-:22])=[O:21]>O1CCCC1.O>[Cl:23][C:8]1[CH:7]=[N:6][CH:5]=[C:4]([Cl:3])[C:9]=1[S:10][C:11]1[S:15][C:14]([C:16]([OH:18])=[O:17])=[CH:13][C:12]=1[N+:20]([O-:22])=[O:21]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 46932421HCID 46932421, compound

Product 1

HCID 602073175-((3,5-Dichloropyridin-4-yl)thio)-4-nitrothiophene-2-carboxylic acidYield 47%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

An aqueous solution of sodium hydroxide (1N, 1.5 mL, 1.5 mmol) was added to a solution of Methyl 5-[(3,5-dichloro-4-pyridyl)sulfanyl]-4-nitro-thiophene-2-carboxylate (0.275 g, 0.75 mmol) in tetrahydrofuran (5 mL), and the resulting mixture was stirred at ambient temperature for 4 hours. After this time the mixture was diluted with water (4.5 mL) and washed the ethyl ether (2×5 mL). The aqueous phase was then acidified to pH 5 by the addition of hydrochloric acid solution (1 M), then the product was extracted into ethyl acetate (5×5 mL), dried (Na2SO4) and the solvent removed under reduced pressure to afford the title product as a white solid (123 mg, 47% yield). 1H NMR (300 MHz, d6-DMSO) δ: 9.0 (2H, s), 8.1 (1H, s). MS m/z: 350.85, 352.90 [M+H]+.

Workup

  1. washwashed the ethyl ether (2×5 mL)
  2. additionThe aqueous phase was then acidified to pH 5 by the addition of hydrochloric acid solution (1 M)
  3. extractionthe product was extracted into ethyl acetate (5×5 mL)
  4. dry with materialdried (Na2SO4)
  5. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-a64d2d6f657e4355a9fb6c14366a28ad
Source dataset
uspto-grants-2014_03
Patent number
US08680139B2

Linked notes

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