Potassium Carbonate → Ethyl 4-[1-(4-chlorobenzyl)-5-fluorobenzimidazol-2-yl]mercaptobutanoate

HRID 1493322Notes

Reaction equation

HRID 1493322 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][N:9]2[C:13]3[CH:14]=[CH:15][C:16]([F:18])=[CH:17][C:12]=3[N:11]=[C:10]2[SH:19])=[CH:4][CH:3]=1.Br[CH2:21][CH2:22][CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][N:9]2[C:13]3[CH:14]=[CH:15][C:16]([F:18])=[CH:17][C:12]=3[N:11]=[C:10]2[S:19][CH2:21][CH2:22][CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 76300Ethyl 4-bromobutyrateHCID 178505424HCID 178505424, compound

Product 1

HCID 14953012Ethyl 4-[1-(4-chlorobenzyl)-5-fluorobenzimidazol-2-yl]mercaptobutanoate

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

9 g of 1-(4-chlorophenylmethyl)-2-mercapto-5-fluorobenzimidazole, prepared in Example 15, and 4.4 ml of ethyl 4-bromobutyrate are refluxed for 5 hours in 100 ml of acetone in the presence of 6.3 g of potassium carbonate. The solvent is evaporated off under vacuum, the residue is taken up in water and then extracted with ethyl acetate and the extract is washed with a dilute solution of sodium hydroxide. The organic phase is dried over magnesium sulfate and evaporated under vacuum to give 11.9 g of ethyl 4-[1-(4-chlorobenzyl)-5-fluorobenzimidazol-2-yl]mercaptobutanoate in the form of an oil, which is used as such for the next step.

Workup

  1. customThe solvent is evaporated off under vacuum
  2. extractionextracted with ethyl acetate
  3. washthe extract is washed with a dilute solution of sodium hydroxide
  4. dry with materialThe organic phase is dried over magnesium sulfate
  5. customevaporated under vacuum

Sources & evidence

ORD record
ord-bdd1d317f4254a85af675631a77bb3f8
Source dataset
uspto-grants-1991_06
Patent number
US05021443

Reaction notes

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