Water → HCID 60207510, compound

HRID 1192279Notes

Reaction equation

HRID 1192279 reaction equation
CC(C)([O-])C.[K+].[Cl:7][C:8]1[CH:13]=[C:12]([Cl:14])[CH:11]=[CH:10][C:9]=1[OH:15].Cl[C:17]1[S:21][C:20]([C:22](=[O:24])[CH3:23])=[CH:19][C:18]=1[N+:25]([O-:27])=[O:26].O>O1CCCC1>[Cl:7][C:8]1[CH:13]=[C:12]([Cl:14])[CH:11]=[CH:10][C:9]=1[O:15][C:17]1[S:21][C:20]([C:22](=[O:24])[CH3:23])=[CH:19][C:18]=1[N+:25]([O-:27])=[O:26]

Participants

6

Reactant 4

HCID 962WaterHCID 84492,4-DichlorophenolHCID 5211051-(5-Chloro-4-nitrothiophen-2-yl)ethan-1-oneHCID 23665647Potassium tert-butoxide

Product 1

HCID 60207510HCID 60207510, compoundYield 55.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Potassium t-butoxide (0.30 g, 2.67 mmol) was suspended in anhydrous tetrahydrofuran (25 mL), 2,4-dichlorophenol (0.40 g, 2.43 mmol) was added and the resulting mixture was stirred at ambient temperature under nitrogen for 30 minutes. After this time, 1-(5-chloro-4-nitro-2-thienyl)ethanone (0.5 g, 2.43 mmol) was added, the resulting mixture was stirred at ambient temperature for 45 minutes, then it was poured into water (100 mL) and stirred at ambient temperature overnight. The resulting solid was collected by filtration, washed with water (2×10 mL) and dried in air. The crude product was dissolved in acetonitrile (7 mL), the resulting solution was evaporated to near dryness and the residue was triturated with diethyl ether (2 mL). The resulting solid was collected by filtration and dried in vacuo at 40° C. overnight to afford the title product as a solid (0.45 g, 55% yield). 1H NMR (300 MHz, d6-acetone) δ: 8.15 (1H, s), 7.68 (1H, d), 7.51 (2H, m), 2.45 (3H, s).

Workup

  1. stirringthe resulting mixture was stirred at ambient temperature for 45 minutes
  2. stirringstirred at ambient temperature overnight
  3. filtrationThe resulting solid was collected by filtration
  4. washwashed with water (2×10 mL)
  5. customdried in air
  6. dissolutionThe crude product was dissolved in acetonitrile (7 mL)
  7. customthe resulting solution was evaporated
  8. customthe residue was triturated with diethyl ether (2 mL)
  9. filtrationThe resulting solid was collected by filtration
  10. customdried in vacuo at 40° C. overnight

Sources & evidence

ORD record
ord-1ac09b7529c64045bb6a45d8671d5d0d
Source dataset
uspto-grants-2014_03
Patent number
US08680139B2

Reaction notes

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