Ethylamine → HCID 86588556, compound

HRID 1796344Notes

Reaction equation

HRID 1796344 reaction equation
[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[C:6](F)[CH:5]=1.Cl.Cl.NC[C:19]1[NH:20][C:21]2[CH:27]=[CH:26][CH:25]=[CH:24][C:22]=2[N:23]=1.[CH2:28]([NH2:30])C>CN1C(=O)CCC1>[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:5]=[CH:6][C:7]([N+:10]([O-:12])=[O:11])=[CH:8][CH:9]=1.[NH2:30][CH2:28][N:20]1[C:21]2[CH:27]=[CH:26][CH:25]=[CH:24][C:22]=2[N:23]=[CH:19]1

Participants

5

Reactant 3

HCID 6341EthylamineHCID 592761Methyl 3-fluoro-4-nitrobenzoateHCID 2723957(1H-benzo[d]imidazol-2-yl)methanamine dihydrochloride

Product 1

HCID 86588556HCID 86588556, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

To a flask under nitrogen atmosphere was charged 500 ml of NMP and 3-fluoro-4 nitro benzoic acid methylester (15.64 g, 78.5 mmol, 1 eq) followed by aminomethyl-benzimidazole dihydrochloride (20.16 g, 91.6 mmol, 1.2 eq). To this, Diispropyl ethylamine (55 ml, 316 mmol, 4 eq) was charged and stirred for 16 hours. The reaction was then poured into 1200 ml of ice water resulting in a yellow/orange solid. The solid was filtered and resuspended in 300 ml of cold water, stirred for 1 hour, filtered and dried to constant weight. Yield 85%, 18.8 g. TLC elution solvent system 5% methanol/95% dichloromethane, Rf=0.6.

Workup

  1. filtrationThe solid was filtered
  2. stirringstirred for 1 hour
  3. filtrationfiltered
  4. customdried to constant weight
  5. washTLC elution solvent system 5% methanol/95% dichloromethane, Rf=0.6

Sources & evidence

ORD record
ord-1c818322919a4ad8a46368921bee7eac
Source dataset
uspto-grants-2006_04
Patent number
US07030150B2

Reaction notes

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