Ethanol → Ethyl 2-amino-1-cyclohexyl-1H-benzo[d]imidazole-5-carboxylate

HRID 2068285Notes

Reaction equation

HRID 2068285 reaction equation
[N:1]#[C:2]Br.O.[CH2:5]([O:7][C:8](=[O:23])[C:9]1[CH:14]=[CH:13][C:12]([NH:15][CH:16]2[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]2)=[C:11]([NH2:22])[CH:10]=1)[CH3:6].C(O)C>C(#N)C>[NH2:1][C:2]1[N:15]([CH:16]2[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21]2)[C:12]2[CH:13]=[CH:14][C:9]([C:8]([O:7][CH2:5][CH3:6])=[O:23])=[CH:10][C:11]=2[N:22]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 962WaterHCID 10476Cyanogen BromideHCID 4068248Ferrostatin-1

Product 1

HCID 67254051Ethyl 2-amino-1-cyclohexyl-1H-benzo[d]imidazole-5-carboxylate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

5 M cyanogen bromide in acetonitrile (2.25 mL) was added to water (25 mL, 1.4 mol) in a 250 mL round bottom flask at room temperature with stirring. To this was added dropwise a solution of 3-amino-4-cyclohexylaminobenzoic acid ethyl ester (2.25 g, 0.00858 mol) in ethanol (25 mL, 0.43 mol) via an additon funnel over 45 minutes. After 3 hours the reaction was concentrated. The residue was dissolved in ethyl acetate and washed with saturated sodium bicarbonate solution then brine. The organic phase was dried over sodium sulfate and concentrated to a dark solid. The solid was triturated with ethanol, filtered and washed with ethanol to give 1.747 g of the title compound as a grayish solid.

Workup

  1. concentrationAfter 3 hours the reaction was concentrated
  2. dissolutionThe residue was dissolved in ethyl acetate
  3. washwashed with saturated sodium bicarbonate solution
  4. dry with materialThe organic phase was dried over sodium sulfate
  5. concentrationconcentrated to a dark solid
  6. customThe solid was triturated with ethanol
  7. filtrationfiltered
  8. washwashed with ethanol

Sources & evidence

ORD record
ord-c7aaefb9149447af9ea20768f0cb2fdc
Source dataset
uspto-grants-2012_10
Patent number
US08293923B2

Reaction notes

Loading…