Ethyl 4-bromobutyrate → Ethyl 4-[(1H-benzimidazol-2-yl)sulfanyl]butanoate

HRID 893353Notes

Reaction equation

HRID 893353 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.[Na].Br[CH2:13][CH2:14][CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17]>C(O)C>[N:3]1[C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[NH:6][C:2]=1[S:1][CH2:13][CH2:14][CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17]

Participants

5

Reactant 3

HCID 76300Ethyl 4-bromobutyrateHCID 5360545SodiumHCID 178527775HCID 178527775, compound

Product 1

HCID 12624992Ethyl 4-[(1H-benzimidazol-2-yl)sulfanyl]butanoateYield 97.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

50 g of 2-mercaptobenzimidazole are dissolved in 300 ml of ethanol, and a solution of 7.65 g of sodium in 150 ml of ethanol is added at room temperature, with stirring. The mixture is stirred for a few minutes at room temperature and 64.3 g of ethyl 4-bromobutyrate are added rapidly. The reaction mixture is refluxed for 6 hours and then cooled. The solvents are evaporated off to dryness under vacuum, the residue is taken up with water and the crystals obtained are filtered off, washed with water and then with ether and dried to give 85 g of ethyl 4-(benzimidazol-2-yl)mercaptobutanoate in the form of crystals melting at 70°-72° C.

Workup

  1. stirringThe mixture is stirred for a few minutes at room temperature
  2. temperatureThe reaction mixture is refluxed for 6 hours
  3. temperaturecooled
  4. customThe solvents are evaporated off to dryness under vacuum
  5. customthe crystals obtained
  6. filtrationare filtered off
  7. washwashed with water
  8. dry with materialwith ether and dried

Sources & evidence

ORD record
ord-428f377e708d49baa00bc0a2df2e7fa7
Source dataset
uspto-grants-1992_06
Patent number
US05124336

Reaction notes

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