Water → HCID 22675463, compound

HRID 1005956Notes

Reaction equation

HRID 1005956 reaction equation
[SH:1][C:2]1[NH:3][C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=1.Br[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][OH:17].C(N(CC)CC)C.O>C(#N)C>[OH:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][S:1][C:2]1[NH:3][C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 1187091-Pentanol, 5-bromo-HCID 178527775HCID 178527775, compound

Product 1

HCID 22675463HCID 22675463, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

1.5 g of 2-mercaptobenzimidazole and 1.7 g of 5-bromopentanol were refluxed for 5 hours in an acetonitrile solvent containing 1.2 g of triethylamine. The reaction mixture was cooled, 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 1.77 g of the title compound (yield: 75%).

Workup

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

Sources & evidence

ORD record
ord-57dc02a48ad746aba98ba3c55459fa03
Source dataset
uspto-grants-2004_09
Patent number
US06787561B1

Reaction notes

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