Dicyclohexylcarbodiimide → HCID 178500069, compound

HRID 976593Notes

Reaction equation

HRID 976593 reaction equation
C1(N=C=NC2CCCCC2)CCCCC1.OC1C2N=NNC=2C=CC=1.[CH3:26][O:27][C:28](=[O:34])[CH2:29][CH2:30][C:31]([O-])=O.[NH2:35][C:36]1[CH:37]=[C:38]([C:43]2[CH:50]=[CH:49][CH:48]=[CH:47][C:44]=2[C:45]#[N:46])[CH:39]=[CH:40][C:41]=1[NH2:42]>CN(C=O)C>[C:45]([C:44]1[CH:47]=[CH:48][CH:49]=[CH:50][C:43]=1[C:38]1[CH:39]=[CH:40][C:41]2[NH:42][C:31]([CH2:30][CH2:29][C:28]([O:27][CH3:26])=[O:34])=[N:35][C:36]=2[CH:37]=1)#[N:46]

Participants

6

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 6930703Mono-Methyl SuccinateHCID 21468845HCID 21468845, compoundHCID 178418300HCID 178418300, compound

Product 1

HCID 178500069HCID 178500069, compoundYield 75.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Dicyclohexylcarbodiimide (0.11 moles, 2.26 g), hydroxybenzotriazole (0.011 moles, 1.48 g) and monomethylsuccinate (0.011 moles, 1.45 g) were dissolved in 75 ml of DMF. 2-(3,4-Diaminophenyl)benzonitrile (0.01 moles, 2.0 g) was added. The reaction was stirred at room temperature for 48 hours The solvent was removed in vacuo. The residue was dissolved in ethyl acetate and washed thoroughly with brine. The ethyl acetate solution was dried over sodium sulfate and filtered. The solvent was removed. The residue was purified by HPLC on silica gel eluted with ethyl acetate. The material was dissolved in 400 ml toluene with 5 mg of p-toluenesulfonic acid and refluxed for 8 hours. The solvent was removed. The residue was purified by HPLC on silica gel eluted with ethyl acetate to yield 2.3 g of methyl 3-[5-(2-cyanophenyl)-1H-benzimidazole-2-yl]propionate. (MS).

Workup

  1. customwas removed in vacuo
  2. dissolutionThe residue was dissolved in ethyl acetate
  3. washwashed thoroughly with brine
  4. dry with materialThe ethyl acetate solution was dried over sodium sulfate
  5. filtrationfiltered
  6. customThe solvent was removed
  7. customThe residue was purified by HPLC on silica gel
  8. washeluted with ethyl acetate
  9. dissolutionThe material was dissolved in 400 ml toluene with 5 mg of p-toluenesulfonic acid
  10. temperaturerefluxed for 8 hours
  11. customThe solvent was removed
  12. customThe residue was purified by HPLC on silica gel
  13. washeluted with ethyl acetate

Sources & evidence

ORD record
ord-51658db947fd4e0484565a6f8ee6c6bf
Source dataset
uspto-grants-1997_03
Patent number
US05612360

Reaction notes

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