Triethylamine → HCID 53719220, compound

HRID 1005519

Reaction equation

HRID 1005519 reaction equation
[OH:1][CH2:2][C:3]1[N:4]([CH2:20][CH3:21])[C:5]([S:11][C:12]2[CH:17]=[C:16]([Cl:18])[CH:15]=[C:14]([Cl:19])[CH:13]=2)=[C:6]([CH:8]([CH3:10])[CH3:9])[N:7]=1.[NH+]1C=CC=CC=1.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(O[C:44]1([O:50][CH2:51][CH2:52][CH2:53][CH3:54])[CH2:49][CH2:48][CH2:47][CH2:46]C1)CCC.C(N(CC)CC)C>C(Cl)Cl>[CH2:51]([O:50][C:44]1([O:1][CH2:2][C:3]2[N:4]([CH2:20][CH3:21])[C:5]([S:11][C:12]3[CH:17]=[C:16]([Cl:18])[CH:15]=[C:14]([Cl:19])[CH:13]=3)=[C:6]([CH:8]([CH3:9])[CH3:10])[N:7]=2)[CH2:46][CH2:47][CH2:48][CH2:49]1)[CH2:52][CH2:53][CH3:54]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 2437181,1-DibutoxycyclohexaneHCID 473933(5-(3,5-Dichlorophenylthio)-1-ethyl-4-isopropyl-1H-imidazol-2-yl)methanolHCID 22033616Pyridinium.p-toluenesulfonate

Product 1

HCID 53719220HCID 53719220, compoundYield 34%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-hydroxymethyl-5-(3,5-dichlorophenylthio)-4-isopropyl-1-ethyl-1H-imidazole (19) (345 mg, 1 mmol) prepared in accordance with the method as described in WO 96/10019 (EXAMPLE 25) and p-toluenesulfonic acid pyridinium (264 mg, 1.05 mmol) in methylene chloride (5 ml) was added 1,1-dibutoxycyclohexane (2.14 g, 10.0 mmol), and stirred at room temperature for 20 hours. A drop of triethylamine was added to the reaction mixture , and the mixture was filtered to remove the precipitated insoluble matter. The filtrate was concentrated under reduced pressure. Hexane was added to the residue, and the mixture was filtered to remove the insoluble matter. The filtrate was purified by chromatography on an alumina column (eluate: toluene) to give the compound 20 (165 mg, 34%). Rf 0.41 (Al2O3 60, Type E, toluene).

Workup

  1. filtrationthe mixture was filtered
  2. customto remove the precipitated insoluble matter
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. additionHexane was added to the residue
  5. filtrationthe mixture was filtered
  6. customto remove the insoluble matter
  7. customThe filtrate was purified by chromatography on an alumina column (eluate: toluene)

Sources & evidence

ORD record
ord-5b3f7ad41dbf4aa48d176520476b5aad
Source dataset
uspto-grants-2000_04
Patent number
US06054591

Linked notes

Loading…