Sodium hydride → 1-[2-(3,4-Dichlorobenzylthio)-4-phenylbutyl]imidazole

HRID 1678986Notes

Reaction equation

HRID 1678986 reaction equation
Cl.Cl[CH:3]([CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH2:4][N:5]1[CH:9]=[CH:8][N:7]=[CH:6]1.[Cl:18][C:19]1[CH:20]=[C:21]([CH:24]=[CH:25][C:26]=1[Cl:27])[CH2:22][SH:23].[H-].[Na+]>O1CCCC1>[Cl:18][C:19]1[CH:20]=[C:21]([CH:24]=[CH:25][C:26]=1[Cl:27])[CH2:22][S:23][CH:3]([CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH2:4][N:5]1[CH:9]=[CH:8][N:7]=[CH:6]1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 1189863,4-Dichlorotoluene-alpha-thiolHCID 203652681-(2-Chloro-4-phenylbutyl)imidazole hydrochloride

Product 1

HCID 203653911-[2-(3,4-Dichlorobenzylthio)-4-phenylbutyl]imidazole

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

600 Mg. of 1-(2-chloro-4-phenylbutyl) imidazole hydrochloride was added to a fully reacted mixture of 1.1 g. of 3,4-dichlorobenzylmercaptan and 400 mg. of 56% sodium hydride dispersion in mineral oil in 30 ml. of tetrahydrofuran. After stirring under reflux for 12 hours the solvent was evaporated under vacuum and 150 ml. of ether was added. The resulting mixture was washed twice with water and the ethereal solution dried and evaporated to afford 1-[2-(3,4-dichlorobenzylthio)-4-phenylbutyl]imidazole, as an oil. This material was converted to the oxalate salt by treatment of an ethereal solution wih oxalic acid in ether until precipitation was complete, which salt was recrystallized from acetone/ethyl acetate as colorless flakes (660 mg.), m.p. 143.5°-146° C.

Workup

  1. temperatureunder reflux for 12 hours the solvent
  2. customwas evaporated under vacuum and 150 ml
  3. additionof ether was added
  4. washThe resulting mixture was washed twice with water
  5. customthe ethereal solution dried
  6. customevaporated

Sources & evidence

ORD record
ord-4409e73bfdb44da1b2b6f1524c4ce588
Source dataset
uspto-grants-1978_03
Patent number
US04078071

Reaction notes

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