Hydrochloric Acid → HCID 14628044, compound

HRID 2165932Notes

Reaction equation

HRID 2165932 reaction equation
[SH:1][C:2]1[NH:3][C:4]2[CH:10]=[C:9]([C:11]([OH:13])=[O:12])[CH:8]=[CH:7][C:5]=2[N:6]=1.[C:14]([C:17]1[CH:27]=[CH:26][C:20]([O:21][CH2:22][CH2:23][CH2:24]Br)=[C:19]([CH2:28][CH2:29][CH3:30])[C:18]=1[OH:31])(=[O:16])[CH3:15].[OH-].[K+].Cl>C(O)C>[C:14]([C:17]1[CH:27]=[CH:26][C:20]([O:21][CH2:22][CH2:23][CH2:24][S:1][C:2]2[NH:3][C:4]3[CH:10]=[C:9]([C:11]([OH:13])=[O:12])[CH:8]=[CH:7][C:5]=3[N:6]=2)=[C:19]([CH2:28][CH2:29][CH3:30])[C:18]=1[OH:31])(=[O:16])[CH3:15]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 27752211-[4-(3-bromopropoxy)-2-hydroxy-3-propylphenyl]ethanoneHCID 178524147HCID 178524147, compound

Product 1

HCID 14628044HCID 14628044, compoundYield 110.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2-mercaptobenzimidazole-5-carboxylic acid (3.25 g), 3-(4-acetyl-3-hydroxy-2-propylphenoxy)propylbromide (2.00 g) and potassium hydroxide (1.27 g) in ethanol (30 ml) was refluxed for 4 hours. Then, the reacting mixture was poured into ice-water, made acidic with concentrated hydrochloric acid and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and then evaporated. The resulting residue was purified by silica gel column chromatography, eluting with dichloromethane-ethyl acetate-methanol (10:2:1), and recrystallized from n-hexane-ethyl acetate to give the title compounds (3.00 g, 67.1%) as pale yellow crystals, mp 106-108 ° C.

Workup

  1. temperaturewas refluxed for 4 hours
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. customevaporated
  5. customThe resulting residue was purified by silica gel column chromatography
  6. washeluting with dichloromethane-ethyl acetate-methanol (10:2:1)
  7. customrecrystallized from n-hexane-ethyl acetate

Sources & evidence

ORD record
ord-989fb45ae3f141daacf9f93dc4c53f6b
Source dataset
uspto-grants-1990_07
Patent number
US04942245

Reaction notes

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