Water → 5-Chloro-2-(5-aminopentylthio)benzimidazole

HRID 1005966Notes

Reaction equation

HRID 1005966 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][N:7]1C(=O)C2=CC=CC=C2C1=O.[Cl:18][C:19]1[CH:28]=[CH:27][C:22]2[N:23]=[C:24]([SH:26])[NH:25][C:21]=2[CH:20]=1.C(N(CC)CC)C.O>C(#N)C>[Cl:18][C:19]1[CH:28]=[CH:27][C:22]2[N:23]=[C:24]([S:26][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][NH2:7])[NH:25][C:21]=2[CH:20]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 136770N-(5-Bromopentyl)phthalimideHCID 178527787HCID 178527787, compound

Product 1

HCID 226754475-Chloro-2-(5-aminopentylthio)benzimidazoleYield 133.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

1.5 g of the compound obtained in Example 17a and 0.93 g of 5-chloro-2-mercaptobenzimidazole were refluxed for 5 hours in 20 ml of acetonitrile containing 0.55 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 obtained residue was purified by silica gel column chromatography (ethyl acetate:hexane) to obtain 1.81 g of the title compound (yield: 91%). Subsequently, the product was added with 0.85 g of hydrazine hydrate and 25 ml of methanol and refluxed for 5 hours. The mixture was cooled to room temperature and then filtered. The filtrate was concentrated, washed with chloroform and then concentrated again to obtain 1 g of the title compound (crude product).

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 obtained residue was purified by silica gel column chromatography (ethyl acetate:hexane)

Sources & evidence

ORD record
ord-0ac98e0776804576bfc7f0000f74121c
Source dataset
uspto-grants-2004_09
Patent number
US06787561B1

Reaction notes

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