Sodium hydride → 1-[4-(4-Chlorophenyl)-2-(4-nitrobenzylthio)-n-butyl]imidazole

HRID 463287Notes

Reaction equation

HRID 463287 reaction equation
Cl[CH:2]([CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=1)[CH2:3][N:4]1[CH:8]=[CH:7][N:6]=[CH:5]1.[N+:18]([C:21]1[CH:28]=[CH:27][C:24]([CH2:25][SH:26])=[CH:23][CH:22]=1)([O-:20])=[O:19].[H-].[Na+]>O1CCCC1>[Cl:17][C:14]1[CH:15]=[CH:16][C:11]([CH2:10][CH2:9][CH:2]([S:26][CH2:25][C:24]2[CH:23]=[CH:22][C:21]([N+:18]([O-:20])=[O:19])=[CH:28][CH:27]=2)[CH2:3][N:4]2[CH:8]=[CH:7][N:6]=[CH:5]2)=[CH:12][CH:13]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 1936194-Nitrobenzyl mercaptanHCID 124320341-[2-Chloro-4-(4-chlorophenyl)butyl]-1H-imidazole

Product 1

HCID 202827561-[4-(4-Chlorophenyl)-2-(4-nitrobenzylthio)-n-butyl]imidazole

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 1.35 g of 1-[2-chloro-4-(4-chlorophenyl)butyl]imidazole and 1.60 g of 4-nitrobenzyl mercaptan in 40 ml tetrahydrofuran was treated with 380 mg of 50% sodium hydride dispersion in mineral oil. After stirring at room temperature for 1 hour and under reflux for 12 hours the solvent was evaporated under vacuum and 50 ml of ether added. The resulting mixture was washed twice with water and the ethereal solution dried (MgSO4) and evaporated. The residue was chromatographed on silica gel eluting with 5% methanol in methylene chloride to give 1-[4-(4-chlorophenyl)-2-(4-nitrobenzylthio)-n-butyl]imidazole.

Workup

  1. temperatureunder reflux for 12 hours the solvent
  2. customwas evaporated under vacuum and 50 ml of ether
  3. additionadded
  4. washThe resulting mixture was washed twice with water
  5. dry with materialthe ethereal solution dried (MgSO4)
  6. customevaporated
  7. customThe residue was chromatographed on silica gel eluting with 5% methanol in methylene chloride

Sources & evidence

ORD record
ord-864bd849a7c0482fb3822c7a52a50120
Source dataset
uspto-grants-1985_05
Patent number
US04518607

Reaction notes

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