Diethyl Malonate → 3-[1-(4-Nitrobenzyl)benzimidazol-2-yl]-2-(carboethoxy)propanoic acid, ethyl ester

HRID 1638560Notes

Reaction equation

HRID 1638560 reaction equation
[Na].C(C(CC)(C([O-])=O)C([O-])=O)C.[H-].[Na+].[C:15]([O:23][CH2:24][CH3:25])(=[O:22])[CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18].[N+:26]([C:29]1[CH:46]=[CH:45][C:32]([CH2:33][N:34]2[C:38]3[CH:39]=[CH:40][CH:41]=[CH:42][C:37]=3[N:36]=[C:35]2[CH2:43]Cl)=[CH:31][CH:30]=1)([O-:28])=[O:27]>CN(C=O)C.C(OCC)(=O)C>[N+:26]([C:29]1[CH:46]=[CH:45][C:32]([CH2:33][N:34]2[C:38]3[CH:39]=[CH:40][CH:41]=[CH:42][C:37]=3[N:36]=[C:35]2[CH2:43][CH:16]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[C:15]([O:23][CH2:24][CH3:25])=[O:22])=[CH:31][CH:30]=1)([O-:28])=[O:27]

Participants

8

Reactant 5

HCID 7761Diethyl MalonateHCID 24758Sodium hydrideHCID 5360545SodiumHCID 69515632,2-DiethylpropanedioateHCID 14722476HCID 14722476, compound

Product 1

HCID 147224773-[1-(4-Nitrobenzyl)benzimidazol-2-yl]-2-(carboethoxy)propanoic acid, ethyl ester

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

The sodium salt of diethylmalonate was generated from 0.35 g of NaH (50% oil dispersion) and 1.1 mL of diethyl malonate in 15 mL of dried DMF with ice cooling. To the above mixture was added 2 g of 1-(4-nitrobenzyl)-2-chloromethylbenzimidazole and the mixture was stirred at room temperature for 18 hours. The reaction mixture was diluted with ethyl acetate, washed with water, dried and concentrated in vacuo. The crude produce was purified by flash column chromatography (hexane/ethyl acetate, 1:1) to give a yellowish thick oil which was crystallized from absolute ethanol to give a white solid; m.p. 135°.

Workup

  1. washwashed with water
  2. customdried
  3. concentrationconcentrated in vacuo
  4. customThe crude produce
  5. customwas purified by flash column chromatography (hexane/ethyl acetate, 1:1)
  6. customto give a yellowish thick oil which
  7. customwas crystallized from absolute ethanol
  8. customto give a white solid

Sources & evidence

ORD record
ord-6fbc542354b249f29e5a898a781a51d8
Source dataset
uspto-grants-1989_11
Patent number
US04880804

Reaction notes

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