Potassium Hydroxide → HCID 14622474, compound

HRID 1639009Notes

Reaction equation

HRID 1639009 reaction equation
[OH-].[K+].[SH:3][C:4]1[NH:5][C:6]2[CH:12]=[CH:11][CH:10]=[CH:9][C:7]=2[N:8]=1.Cl[CH:14](Cl)[C:15]1[C:24]2[C:19](=[CH:20][C:21]([O:31][CH3:32])=[C:22]([O:25][CH2:26][C:27]([F:30])([F:29])[F:28])[CH:23]=2)[CH2:18][CH2:17][N:16]=1>CCO.C(Cl)Cl>[CH3:32][O:31][C:21]1[CH:20]=[C:19]2[C:24](=[CH:23][C:22]=1[O:25][CH2:26][C:27]([F:30])([F:28])[F:29])[C:15]([CH2:14][S:3][C:4]1[NH:5][C:6]3[CH:12]=[CH:11][CH:10]=[CH:9][C:7]=3[N:8]=1)=[N:16][CH:17]=[CH:18]2

Participants

6

Reactant 3

HCID 14797Potassium HydroxideHCID 14622449HCID 14622449, compoundHCID 178527775HCID 178527775, compound

Product 1

HCID 14622474HCID 14622474, compoundYield 60.4%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 514.8 mg of 86% KOH (7.87 mmol) in 20 ml of 99% EtOH were added 434.1 mg of 2-mercaptobenzimidazole (II-1) (2.89 mmol) and 900.1 mg of 1-dichloromethyl-6-methoxy-7-(2,2,2-trifluoroethoxy)-3,4-dihydroisoquinoline (IV-1) (2.63 mmol) in order. After stirring for 30 min. at room temperature, the mixture was refluxed for 3 hr. and concentrated under reduced pressure. The residue was mixed with water and extracted with CHCl3. The objective compound existing as an insoluble material was filtered and combined with CHCl3 extract to give 722.5 mg of the crude product. It was dispersed in 15 ml of CH2Cl2, filtered and washed with CH2Cl2 to give 666.5 mg of the titled compound 2-{[6-methoxy-7-(2,2,2-trifluoroethoxy)isoquinolin-1-yl]methylthio}-benzimidazole (Ia-7) (Yield: 60.4%).

Workup

  1. temperaturethe mixture was refluxed for 3 hr
  2. concentrationand concentrated under reduced pressure
  3. additionThe residue was mixed with water
  4. extractionextracted with CHCl3
  5. filtrationwas filtered
  6. extractionextract
  7. customto give 722.5 mg of the crude product
  8. filtrationfiltered
  9. washwashed with CH2Cl2

Sources & evidence

ORD record
ord-8885082bd95246b8880644c6c16c6c02
Source dataset
uspto-grants-1989_11
Patent number
US04882338

Reaction notes

Loading…