Potassium Hydroxide → HCID 60207316, compound

HRID 1192072Notes

Reaction equation

HRID 1192072 reaction equation
[OH-].[K+].[Cl:3][C:4]1[C:9]([Cl:10])=[CH:8][CH:7]=[CH:6][C:5]=1[S:11][C:12]1[S:16][C:15]([C:17]([O:19]CC)=[O:18])=[CH:14][C:13]=1[N+:22]([O-:24])=[O:23]>O>[Cl:3][C:4]1[C:9]([Cl:10])=[CH:8][CH:7]=[CH:6][C:5]=1[S:11][C:12]1[S:16][C:15]([C:17]([OH:19])=[O:18])=[CH:14][C:13]=1[N+:22]([O-:24])=[O:23]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 46932330HCID 46932330, compound

Product 1

HCID 60207316HCID 60207316, compoundYield 26.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A solution of potassium hydroxide (72 mg, 1.27 mmol) in water (3.5 mL) was added to a suspension of ethyl 5-(2,3-dichlorophenylsulfanyl)-4-nitrothiophene-2-carboxylate (0.24 g, 0.63 mmol) in IMS (2 mL) and the resulting mixture was stirred at ambient temperature for 72 hours. After this time the mixture was diluted with water (4.5 mL) and washed the diethyl ether (2×5 mL). The aqueous phase was then acidified to pH 1 by the addition of 20% hydrochloric acid. The oil formed which solidified after stirring for 2 minutes. The mixture was left to stir for 1 hour then the solid was collected by filtration, washed with water (3×2 mL) and dried in vacuo at 40° C. overnight. The crude solid was absorbed onto silica and purified by chromatography over silica using ethyl acetate as eluent. The fractions containing the product were collected and the solvent removed under reduced pressure. The resulting solid was triturated with a small volume of diethyl ether, collected by filtration and dried in vacuo at 40° C. overnight to afford the title product as a yellow solid (58 mg, 26% yield). 1H NMR (d6-DMSO) δ: 8.08 (1H, s), 8.00 (2H, m), 7.64 (1H, m).

Workup

  1. washwashed the diethyl ether (2×5 mL)
  2. additionThe aqueous phase was then acidified to pH 1 by the addition of 20% hydrochloric acid
  3. customThe oil formed which
  4. stirringafter stirring for 2 minutes
  5. waitThe mixture was left
  6. stirringto stir for 1 hour
  7. filtrationthe solid was collected by filtration
  8. washwashed with water (3×2 mL)
  9. customdried in vacuo at 40° C. overnight
  10. customThe crude solid was absorbed onto silica
  11. custompurified by chromatography over silica
  12. additionThe fractions containing the product
  13. customwere collected
  14. customthe solvent removed under reduced pressure
  15. customThe resulting solid was triturated with a small volume of diethyl ether
  16. filtrationcollected by filtration
  17. customdried in vacuo at 40° C. overnight

Sources & evidence

ORD record
ord-db5ca27fce464db1ac9158b5ceeab0ab
Source dataset
uspto-grants-2014_03
Patent number
US08680139B2

Reaction notes

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