4-Nitrobenzenethiol → HCID 178526721, compound

HRID 744078Notes

Reaction equation

HRID 744078 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.Cl[CH2:15][CH2:16][C:17]1[N:18]=[CH:19][NH:20][CH:21]=1>CN(C)C=O.[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[N+:3]([C:6]1[CH:11]=[CH:10][C:9]([S:12][CH2:15][CH2:16][C:17]2[N:18]=[CH:19][NH:20][CH:21]=2)=[CH:8][CH:7]=1)([O-:5])=[O:4]

Participants

6

Reactant 3

HCID 158094-NitrobenzenethiolHCID 24758Sodium hydrideHCID 1784785704-(2-chloroethyl)-1H-imidazole hydrochloride

Product 1

HCID 178526721HCID 178526721, compound

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 6228DimethylformamideSolvent

Procedure

200 mg (60% in oil, 5 mmol) of sodium hydride are added to a solution of 1.86 g (12 mmol) of 4-nitrothiophenol in 10 ml of dimethylformamide. The mixture is stirred at room temperature for 1 hour under nitrogen. 200 g (1.2 mmol) of 4-(2-chloroethyl)-1H-imidazole hydrochloride and tetrabutylammonium iodide (catalytic amount) are then added. The mixture is heated for 1 day at 80° C. and then the solvent is evaporated under reduced pressure. The residue is stirred in diethyl ether and filtered. Dilute hydrochloric acid is added to the filtrate and the excess 4-nitrothiophenol is removed by extracting with diethyl ether. The aqueous solution is basified with potassium carbonate and then the title compound is extracted with chloroform and crystallized from ethanol, M.p.: 167°-168° C.

Workup

  1. temperatureThe mixture is heated for 1 day at 80° C.
  2. customthe solvent is evaporated under reduced pressure
  3. stirringThe residue is stirred in diethyl ether
  4. filtrationfiltered
  5. additionDilute hydrochloric acid is added to the filtrate
  6. customthe excess 4-nitrothiophenol is removed
  7. extractionby extracting with diethyl ether
  8. extractionthe title compound is extracted with chloroform
  9. customcrystallized from ethanol, M.p.: 167°-168° C.

Sources & evidence

ORD record
ord-9cbce880acb54e86ac26a4f6e2ff919e
Source dataset
uspto-grants-1996_09
Patent number
US05559113

Reaction notes

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