Hydrochloric Acid → HCID 178460783, compound

HRID 860948Notes

Reaction equation

HRID 860948 reaction equation
[CH2:1](I)[CH2:2][CH3:3].[SH:5][C:6]1[N:10]([CH2:11][C:12]2[CH:17]=[CH:16][C:15]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[C:24]3[NH:28][N:27]=[N:26][N:25]=3)=[CH:14][CH:13]=2)[C:9]2[C:29]([C:33]([O:35][CH2:36][CH3:37])=[O:34])=[CH:30][CH:31]=[CH:32][C:8]=2[N:7]=1.[OH-].[Na+].Cl>C(O)C>[CH2:1]([S:5][C:6]1[N:10]([CH2:11][C:12]2[CH:13]=[CH:14][C:15]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[C:24]3[NH:28][N:27]=[N:26][N:25]=3)=[CH:16][CH:17]=2)[C:9]2[C:29]([C:33]([O:35][CH2:36][CH3:37])=[O:34])=[CH:30][CH:31]=[CH:32][C:8]=2[N:7]=1)[CH2:2][CH3:3]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 336431-IodopropaneHCID 178468775HCID 178468775, compound

Product 1

HCID 178460783HCID 178460783, compoundYield 40.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Propyl iodide (0.37 g) was added to a solution of ethyl 2-mercapto-1-[[2′-(1H-tetrazol-5-yl)biphenyl-4-yl]methyl]benzimidazole-7-carboxylate (0.91 g) in ethanol (13 ml) containing 1N NaOH (4.0 ml) and the mixture was stirred at room temperature for 5 hours. The reaction mixture was adjusted to about pH 4 with dilute hydrochloric acid to give crystals. The crystals were collected by filtration and purified by column chromatography on silica gel. Recrystallization from ethyl acetate-hexane gave colorless prisms (0.4 g, 40%), m.p. 177–178° C. (decomp.).

Workup

  1. customto give crystals
  2. filtrationThe crystals were collected by filtration
  3. custompurified by column chromatography on silica gel
  4. customRecrystallization from ethyl acetate-hexane

Sources & evidence

ORD record
ord-514190edbb554a57a6f795edd0d7f9d5
Source dataset
uspto-grants-2006_12
Patent number
US07153972B2

Reaction notes

Loading…