1,3-Dibromobenzene → 1-(3-Bromophenyl)-4-nitrobenzimidazole

HRID 742340Notes

Reaction equation

HRID 742340 reaction equation
[N+:1]([C:4]1[C:12]2[NH:11][CH:10]=[N:9][C:8]=2[CH:7]=[CH:6][CH:5]=1)([O-:3])=[O:2].[Br:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16](Br)[CH:15]=1.C(=O)([O-])[O-].[K+].[K+]>CN1CCCC1=O>[Br:13][C:14]1[CH:15]=[C:16]([N:9]2[C:8]3[CH:7]=[CH:6][CH:5]=[C:4]([N+:1]([O-:3])=[O:2])[C:12]=3[N:11]=[CH:10]2)[CH:17]=[CH:18][CH:19]=1

Participants

5

Reactant 3

HCID 79271,3-Dibromobenzene2×HCID 11430Potassium CarbonateHCID 178526550HCID 178526550, compound

Product 1

HCID 194260051-(3-Bromophenyl)-4-nitrobenzimidazole

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
140 °C

Procedure

4-Nitrobenzimidazole (see Example 19. 0.75 g, 4.6 mmol), 1,3-dibromobenzene (1.11 ml, 9.2 mmol), potassium carbonate (0.64 g, 4.6 mmol) and a catalytic amount of Cu-bronze were mixed in dry 1-methyl-2-pyrrolidone (2 ml) and heated to 140° C. for 3 days. One equivalent of 1,3-dibromobenzene was added and heating was continued for 24 hours. The cooled reaction mixture was extracted with ethyl acetate. The extract was dried and concentrated and eluted through silica gel with ethyl acetate/methanol (9:1) to yield 7 g (33 mg, mp 180°-182° C.).

Workup

  1. temperatureheating
  2. customThe cooled reaction mixture
  3. extractionwas extracted with ethyl acetate
  4. customThe extract was dried
  5. concentrationconcentrated
  6. washeluted through silica gel with ethyl acetate/methanol (9:1)
  7. customto yield 7 g (33 mg, mp 180°-182° C.)

Sources & evidence

ORD record
ord-c39482b417884cc5be24fe4606818bce
Source dataset
uspto-grants-1996_09
Patent number
US05554630

Reaction notes

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