Sodium Carbonate → 7-Bromo-5-chloro-1H-benzimidazole

HRID 1024041Notes

Reaction equation

HRID 1024041 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[C:4]([NH2:9])[C:3]=1[NH2:10].[C:11]([O-])([O-])=O.[Na+].[Na+]>C(O)=O>[Br:1][C:2]1[C:3]2[N:10]=[CH:11][NH:9][C:4]=2[CH:5]=[C:6]([Cl:8])[CH:7]=1

Participants

4

Reactant 2

HCID 10340Sodium CarbonateHCID 3515293-Bromo-5-chlorobenzene-1,2-diamine

Product 1

HCID 866841377-Bromo-5-chloro-1H-benzimidazoleYield 77%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 109b (4.3 g, 19.5 mmol) in formic acid (10 mL) was heated at 80° C. for 1 h. After cooled to room temperature, the reaction mixture was poured into aqueous Na2CO3 (30 mL) and the mixture was extracted with ethyl acetate (30 mL×3). The combined organic phase was dried over anhydrous Na2SO4, filtered, and evaporated under reduced pressure to afford 109c as a brown solid (3.5 g, 77%). LCMS: [M+H]+ 233. 1H NMR (500 MHz, CDCl3) δ 10.05 (bs, 1H), 8.18 (s, 1H), 7.64 (bs, 1H), 7.50 (s, 1H).

Workup

  1. temperatureAfter cooled to room temperature
  2. extractionthe mixture was extracted with ethyl acetate (30 mL×3)
  3. dry with materialThe combined organic phase was dried over anhydrous Na2SO4
  4. filtrationfiltered
  5. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-6d6cbca6595d4b66aa59085527c591bd
Source dataset
uspto-grants-2014_05
Patent number
US08722676B2

Reaction notes

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