Water → 2-(2-Aminoethylthio)-4,5-diphenylimidazole

HRID 362893Notes

Reaction equation

HRID 362893 reaction equation
[H-].[Na+].[C:3]1([C:9]2[N:10]=[C:11]([SH:20])[NH:12][C:13]=2[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.Br.Br[CH2:23][CH2:24][NH2:25].O>C1COCC1>[NH2:25][CH2:24][CH2:23][S:20][C:11]1[NH:10][C:9]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=2)=[C:13]([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[N:12]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 27742172-Bromoethylamine hydrobromideHCID 178527825HCID 178527825, compound

Product 1

HCID 289159662-(2-Aminoethylthio)-4,5-diphenylimidazoleYield 51.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

60% NaH in oil (0.91 g, 22.8 mmol) was added to a suspension of 4,5-diphenyl-2-imidazolethiol (2.5 g, 9.9 mmol) in dry THF (80 ml) at room temperature under stirring. After 15 minutes, 2-bromoethylamine hydrobromide (2.0 g, 9.9 mmol) was added to the mixture. The reaction mixture was refluxed for 1 hour, then poured into water (500 ml) and extracted with ethyl acetate. The extract was dried (MgSO4) and concentrated. The residue was recrystallized (toluene) to give 2-(2-aminoethylthio)-4,5-diphenylimidazole (51.3%): mp 152°-154° C.

Workup

  1. temperatureThe reaction mixture was refluxed for 1 hour
  2. extractionextracted with ethyl acetate
  3. dry with materialThe extract was dried (MgSO4)
  4. concentrationconcentrated
  5. customThe residue was recrystallized (toluene)

Sources & evidence

ORD record
ord-e93c12e45e254abfa816f6154a42db91
Source dataset
uspto-grants-1999_02
Patent number
US05872115

Reaction notes

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