4-Nitrobenzenethiol → HCID 46932053, compound

HRID 1192037Notes

Reaction equation

HRID 1192037 reaction equation
[H-].[Na+].[N+:3]([C:6]1[CH:11]=[CH:10][C:9]([SH:12])=[CH:8][CH:7]=1)([O-:5])=[O:4].Cl[C:14]1[S:18][C:17]([C:19](=[O:21])[CH3:20])=[CH:16][C:15]=1[N+:22]([O-:24])=[O:23]>O>[N+:22]([C:15]1[CH:16]=[C:17]([C:19](=[O:21])[CH3:20])[S:18][C:14]=1[S:12][C:9]1[CH:10]=[CH:11][C:6]([N+:3]([O-:5])=[O:4])=[CH:7][CH:8]=1)([O-:24])=[O:23]

Participants

5

Reactant 3

HCID 158094-NitrobenzenethiolHCID 24758Sodium hydrideHCID 5211051-(5-Chloro-4-nitrothiophen-2-yl)ethan-1-one

Product 1

HCID 46932053HCID 46932053, compoundYield 38.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Anhydrous N,N-dimethylformide (5 mL) was degassed with nitrogen for 30 minutes then sodium hydride (60% dispersion in mineral oil, 0.11 g, 2.75 mmol) was added. 4-Nitrobenzenethiol (0.38 g, 2.43 mmol) was added in portions at ambient temperature and the resulting mixture was stirred at ambient temperature under nitrogen for 20 minutes. Then 1-(5-chloro-4-nitro-2-thienyl)ethanone (0.5 g, 2.43 mmol) was added and the reaction mixture was stirred at ambient temperature overnight under nitrogen. The reaction mixture was diluted with water (40 mL) and stirred for 30 minutes. The precipitated solid was collected by filtration and washed with water (2×4 mL). The crude solid was recrystallised from acetonitrile (12 mL) to afford the title compound as a brown solid (0.302 g, 38% yield). 1H NMR (300 MHz, CDCl3) δ: 8.38 (2H, d, J=8.85 Hz), 8.09 (1H, s), 7.89 (2H, d, J=8.85 Hz), 2.50 (3H, s).

Workup

  1. customAnhydrous N,N-dimethylformide (5 mL) was degassed with nitrogen for 30 minutes
  2. stirringthe reaction mixture was stirred at ambient temperature overnight under nitrogen
  3. stirringstirred for 30 minutes
  4. filtrationThe precipitated solid was collected by filtration
  5. washwashed with water (2×4 mL)
  6. customThe crude solid was recrystallised from acetonitrile (12 mL)

Sources & evidence

ORD record
ord-9eb9b53d9c694ef0a77f1c4d782102ab
Source dataset
uspto-grants-2014_03
Patent number
US08680139B2

Reaction notes

Loading…