Dicyclohexylcarbodiimide → HCID 178502027, compound

HRID 2367083Notes

Reaction equation

HRID 2367083 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:9]([C:11]2[CH:20]=[CH:19][CH:18]=[CH:17][C:12]=2[C:13]([O:15][CH3:16])=[O:14])=[O:10])[CH:5]=[CH:6][C:7]=1[NH2:8].[CH3:21][O:22][C:23]([N:25]=[C:26]=S)=[O:24].C1CCC(N=C=NC2CCCCC2)CC1>C(#N)C.C1C=CC=CC=1>[CH3:21][O:22][C:23]([NH:25][C:26]1[NH:8][C:7]2[CH:6]=[CH:5][C:4]([C:9]([C:11]3[CH:20]=[CH:19][CH:18]=[CH:17][C:12]=3[C:13]([O:15][CH3:16])=[O:14])=[O:10])=[CH:3][C:2]=2[N:1]=1)=[O:24]

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 552246Methoxycarbonyl isothiocyanateHCID 67044285Methyl 2-[(3,4-diaminophenyl)carbonyl]benzoate

Product 1

HCID 178502027HCID 178502027, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 21919336Acetonitrile benzeneSolvent

Procedure

To a solution of methyl 2-[(3,4-diaminophenyl)carbonyl]benzoate (134 mg, 0.50 mmol) in a mixture of acetonitrile-benzene (1:1, 5 mL) methyl isothiocyanatidocarbonate (70 mg, 0.60 mmol) was added followed by the addition of DCC (153 mg, 0.75 mmol) and the reaction mixture was heated to reflux for 18 h. After cooling to room temperature the reaction mixture was concentrated. The residue was triturated with diethyl ether (2×, 10 mL) and the pale orange solid was collected by filtration to give methyl 2-[(2-{[(methoxy)carbonyl]amino}-1H-benzimidazol-5-yl)carbonyl]benzoate (125 mg, 71%). MS (EI) for C18H15N3O5: 354 (MH+).

Workup

  1. additionwas added
  2. temperaturethe reaction mixture was heated
  3. temperatureto reflux for 18 h
  4. concentrationwas concentrated
  5. customThe residue was triturated with diethyl ether (2×, 10 mL)
  6. filtrationthe pale orange solid was collected by filtration

Sources & evidence

ORD record
ord-d01bd7b198ca40ab839d206b3dad0cb3
Source dataset
uspto-grants-2014_04
Patent number
US08697737B2

Reaction notes

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