Hydrochloric Acid → Ethyl 4-[1-(4-chlorobenzyl)-5-fluorobenzimidazol-2-yl]-3,3-dimethylbutanoate

HRID 1493324Notes

Reaction equation

HRID 1493324 reaction equation
[Cl:1][C:2]1[CH:17]=[CH:16][C:5]([CH2:6][NH:7][C:8]2[CH:14]=[CH:13][C:12]([F:15])=[CH:11][C:9]=2[NH2:10])=[CH:4][CH:3]=1.[CH3:18][CH:19]=C(C)C.[CH3:23][C:24]([CH3:33])([CH2:29][C:30](O)=O)[CH2:25][C:26]([OH:28])=[O:27].Cl>C(Cl)(Cl)Cl.C(O)C.C(N(CC)CC)C>[Cl:1][C:2]1[CH:17]=[CH:16][C:5]([CH2:6][N:7]2[C:8]3[CH:14]=[CH:13][C:12]([F:15])=[CH:11][C:9]=3[N:10]=[C:30]2[CH2:29][C:24]([CH3:23])([CH3:33])[CH2:25][C:26]([O:28][CH2:18][CH3:19])=[O:27])=[CH:4][CH:3]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 105532-Methyl-2-butene2×HCID 209843,3-Dimethylglutaric acidHCID 149529912-(4-Chlorobenzylamino)-5-fluoroaniline

Product 1

HCID 14953020Ethyl 4-[1-(4-chlorobenzyl)-5-fluorobenzimidazol-2-yl]-3,3-dimethylbutanoate

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 6212ChloroformSolvent2×HCID 8471TriethylamineSolvent

Procedure

10 g of 2-(4-chlorobenzylamino)-5-fluoroaniline, prepared in Example 8, are dissolved in 100 ml of chloroform, stabilized with amylene, and 6 ml of triethylamine. A solution of 8.25 g of the acid chloride ethyl ester of 3,3-dimethylglutaric acid, prepared in Example 28, in 20 ml of chloroform, stabilized with amylene, is added dropwise. The mixture is stirred for two hours at room temperature, the crystals formed are filtered off and the solvents are evaporated off under vacuum. The residue obtained is dissolved in 200 ml of ethanol and 30 ml of concentrated hydrochloric acid and the mixture is refluxed for 10 hours. The solvents are evaporated off to dryness and the residue is taken up with water and then extracted with ethyl acetate. The organic phase is dried and evaporated under vacuum to give 14 g of ethyl 4-[1-(4-chlorobenzyl)-5-fluorobenzimidazol-2-yl]-3,3-dimethylbutanoate in the form of an oil, which is used as such for the next step.

Workup

  1. additionis added dropwise
  2. customthe crystals formed
  3. filtrationare filtered off
  4. customthe solvents are evaporated off under vacuum
  5. customThe residue obtained
  6. customThe solvents are evaporated off to dryness
  7. extractionextracted with ethyl acetate
  8. customThe organic phase is dried
  9. customevaporated under vacuum

Sources & evidence

ORD record
ord-e1be63b5493f4e0293dd645a40201e42
Source dataset
uspto-grants-1991_06
Patent number
US05021443

Reaction notes

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