2-Chlorobenzimidazole → HCID 86694205, compound

HRID 707347Notes

Reaction equation

HRID 707347 reaction equation
[N+:1]([C:4]1[C:5]([NH:10][CH:11]2[CH2:16][CH2:15][CH:14]([NH2:17])[CH2:13][CH2:12]2)=[N:6][CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].Cl[C:19]1[NH:23][C:22]2[CH:24]=[CH:25][CH:26]=[CH:27][C:21]=2[N:20]=1>CN1CCCC1=O.O>[NH:20]1[C:21]2[CH:27]=[CH:26][CH:25]=[CH:24][C:22]=2[N:23]=[C:19]1[NH:17][CH:14]1[CH2:15][CH2:16][CH:11]([NH:10][C:5]2[C:4]([N+:1]([O-:3])=[O:2])=[CH:9][CH:8]=[CH:7][N:6]=2)[CH2:12][CH2:13]1

Participants

5

Reactant 2

HCID 785722-ChlorobenzimidazoleHCID 22591412HCID 22591412, compound

Product 1

HCID 86694205HCID 86694205, compoundYield 53.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
180 °C

Procedure

A mixture of N1-(3-nitropyridin-2-yl)cyclohexane-1,4-diamine (500 mg, 2.11 mmol) and 2-chloro-1H-benzoimidazole (320 mg, 2.11 mmol) in N-methylpyrrolidinone (5 mL) was heated at 180° C. in microwave for 2 hours. The mixture was diluted with water (60 mL), and extracted with ethyl acetate (2×50 mL). The organic layer was dried over sodium sulfate and concentrated to give N1-(1H-benzo[d]imidazol-2-yl)-N4-(3-nitropyridin-2-yl)cyclohexane-1,4-diamine (400 mg, 1.13 mmol, 53.8% yield) which was used in the next step without further purification.

Workup

  1. extractionextracted with ethyl acetate (2×50 mL)
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-56a18bb87cc44d4a82b30b1f4dee6bd5
Source dataset
uspto-grants-2015_11
Patent number
US09174992B2

Reaction notes

Loading…