Hydrochloric Acid → 1H-Imidazole-2-methanol, 5-((3,5-dichlorophenyl)thio)-4-(1-methylethyl)-1-(2-(2-pyridinyl)ethyl)-

HRID 1857747Notes

Reaction equation

HRID 1857747 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([S:9][C:10]2[N:14]([CH2:15][CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=3)[C:13]([CH2:23][O:24]CC3C=CC(OC)=CC=3)=[N:12][C:11]=2[CH:34]([CH3:36])[CH3:35])[CH:5]=[C:6]([Cl:8])[CH:7]=1.Cl>C(O)C>[Cl:8][C:6]1[CH:5]=[C:4]([S:9][C:10]2[N:14]([CH2:15][CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=3)[C:13]([CH2:23][OH:24])=[N:12][C:11]=2[CH:34]([CH3:36])[CH3:35])[CH:3]=[C:2]([Cl:1])[CH:7]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 22130372HCID 22130372, compound

Product 1

HCID 4740461H-Imidazole-2-methanol, 5-((3,5-dichlorophenyl)thio)-4-(1-methylethyl)-1-(2-(2-pyridinyl)ethyl)-Yield 51.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
90 °C

Procedure

To 1.43 g of 5-(3,5-dichlorophenylthio)-4-isopropyl-2-(p-methoxybenzyloxymethyl)-1-(2-(2-pyridyl)ethyl)-1H-imidazole was added 20 ml of ethanol and 40 ml of 36% hydrochloric acid, and the mixture was stirred at 90° C. for 2 hours. After completion of the reaction, the solvent was distilled off under reduced pressure, an aqueous sodium hydrogen carbonate solution was added, and extracted with ethyl acetate. The extract was dried over sodium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel chromatography (ethyl acetate:methanol=10:1) to give 571 mg of 5-(3,5-dichlorophenylthio)-4-isopropyl-2-hydroxymethyl-1-(2-(2-pyridyl)ethyl)-1H-imidazole (112a) (yield 51%). 1H-NMR (CDCl3 -TMS) δ ppm: 1.29(d,J=6.8 Hz,6H), 3.15(m,3H), 4.52 (m,2H), 4.76(s,2H), 6.87(d,2H), 6.80-7.40(m,3H), 7.60(m,1H),8.50(m,1H); Elementary analysis (C20H21Cl2N3OS); Calc. (%): C,56.87;H,5.01;N,9.95;Cl,16.79;S,7.59; Found (%): C,56.58;H,5.13;N,9.90;Cl,16.65;S,7.53.

Workup

  1. customAfter completion of the reaction
  2. distillationthe solvent was distilled off under reduced pressure
  3. additionan aqueous sodium hydrogen carbonate solution was added
  4. extractionextracted with ethyl acetate
  5. dry with materialThe extract was dried over sodium sulfate
  6. distillationthe solvent was distilled off under reduced pressure
  7. customThe residue was purified by silica gel chromatography (ethyl acetate:methanol=10:1)

Sources & evidence

ORD record
ord-ef58d726592d4f408839a79c777878dc
Source dataset
uspto-grants-2000_11
Patent number
US06147097

Reaction notes

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