Water → 5-Chloro-2-(5-(2-pyridyloxy)pentylthio)benzimidazole

HRID 1005955Notes

Reaction equation

HRID 1005955 reaction equation
S(O[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][O:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=1)(C1C=CC(C)=CC=1)(=O)=O.[Cl:24][C:25]1[CH:34]=[CH:33][C:28]2[N:29]=[C:30]([SH:32])[NH:31][C:27]=2[CH:26]=1.C(N(CC)CC)C.O>C(#N)C>[Cl:24][C:25]1[CH:34]=[CH:33][C:28]2[N:29]=[C:30]([S:32][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][O:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=3)[NH:31][C:27]=2[CH:26]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 121371192-(5-Tosyloxy-pentyloxy)pyridineHCID 178527787HCID 178527787, compound

Product 1

HCID 121371205-Chloro-2-(5-(2-pyridyloxy)pentylthio)benzimidazoleYield 42%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

0.67 g of the compound obtained in Example 3b and 0.37 g of 5-chloro-2-mercaptobenzimidazole were refluxed for 5 hours in 15 ml of acetonitrile containing 0.25 g of triethylamine. The reaction mixture was cooled to room temperature, then added with water and extracted with ethyl acetate. The extract was dried over sodium sulfate and the solvent was evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography (ethyl acetate:hexane) to obtain 0.25 g of the title compound (yield: 42%).

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe extract was dried over sodium sulfate
  3. customthe solvent was evaporated under reduced pressure
  4. customThe resulting residue was purified by silica gel column chromatography (ethyl acetate:hexane)

Sources & evidence

ORD record
ord-a0a782bd816b4f42b245bfcaa813e2dd
Source dataset
uspto-grants-2004_09
Patent number
US06787561B1

Reaction notes

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