Triethylamine → HCID 18791978, compound

HRID 1005521Notes

Reaction equation

HRID 1005521 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([S:9][C:10]2[N:14]([CH3:15])[C:13]([CH2:16][CH2:17][OH:18])=[N:12][C:11]=2[CH:19]([CH3:21])[CH3:20])[CH:5]=[C:6]([Cl:8])[CH:7]=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH3:34][O:35][C:36]1(OC)[CH:43]2[CH2:44][CH:39]3[CH2:40][CH:41]([CH2:45][CH:37]1[CH2:38]3)[CH2:42]2.C(N(CC)CC)C>O1CCCC1.C1(C)C=CC=CC=1>[Cl:8][C:6]1[CH:5]=[C:4]([S:9][C:10]2[N:14]([CH3:15])[C:13]([CH2:16][CH2:17][O:18][C:36]3([O:35][CH3:34])[CH:43]4[CH2:44][CH:39]5[CH2:40][CH:41]([CH2:45][CH:37]3[CH2:38]5)[CH2:42]4)=[N:12][C:11]=2[CH:19]([CH3:21])[CH3:20])[CH:3]=[C:2]([Cl:1])[CH:7]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 4740102-(5-(3,5-Dichlorophenylthio)-4-isopropyl-1-methyl-1H-imidazol-2-yl)ethanolHCID 521998p-Toluenesulfonic acid monohydrateHCID 114355322,2-dimethoxyadamantane

Product 1

HCID 18791978HCID 18791978, compoundYield 44.6%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 5-(3,5-dichlorophenylthio)-4-isopropyl-2-(2-hydroxyethyl)-1-methyl-1H-imidazole (22) (345 mg, 1 mmol) prepared in accordance with the method as described in WO 96/10019 and p-toluenesulfonic acid mono hydrate (200 mg) in a mixture of tetrahydrofuran (5 mL) - toluene (50 mL) was concentrated under reduced pressure. The residue was dried with a vacuum pump on an oil bath at 50° C. for 40 minutes. The residue was dissolved in toluene (10 mL), and cooled on an ice-bath under nitrogen atmosphere. Then a solution of 2,2-dimethoxyadamantane (1.93 g, 10 mmol) in toluene (1 mL) was added thereto. After stirring at the same temperature for 30 minutes, the reaction mixture was further stirred at room temperature for 4 hours without ice-bath. Triethylamine (0.17 mL, 1.25 mmol) was added to the reaction mixture, and the reaction mixture was concentrated under reduced pressure. Hexane was added to the residue and filtered off the insoluble matter. The hexane-soluble matter was purified by chromatography on an alumina column (eluate: hexane - ethyl acetate (2:1)) to give the compound 23 (227 mg, 44%). Mp 74.5-76° C.

Workup

  1. concentrationwas concentrated under reduced pressure
  2. customThe residue was dried with a vacuum pump on an oil bath at 50° C. for 40 minutes
  3. dissolutionThe residue was dissolved in toluene (10 mL)
  4. temperaturecooled on an ice-bath under nitrogen atmosphere
  5. stirringthe reaction mixture was further stirred at room temperature for 4 hours without ice-bath
  6. concentrationthe reaction mixture was concentrated under reduced pressure
  7. additionHexane was added to the residue
  8. filtrationfiltered off the insoluble matter
  9. customThe hexane-soluble matter was purified by chromatography on an alumina column (eluate: hexane - ethyl acetate (2:1))

Sources & evidence

ORD record
ord-c74cdded1e004facabe193c56130077e
Source dataset
uspto-grants-2000_04
Patent number
US06054591

Reaction notes

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