Sodium Bicarbonate → HCID 178422430, compound

HRID 475198Notes

Reaction equation

HRID 475198 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([NH2:8])[C:5]([NH2:9])=[C:4]([CH3:10])[CH:3]=1.[C:11]([O-])(O)=O.[Na+]>C(O)=O>[Br:1][C:2]1[CH:3]=[C:4]([CH3:10])[C:5]2[NH:9][CH:11]=[N:8][C:6]=2[CH:7]=1

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 15163975-Bromo-3-methylbenzene-1,2-diamine

Product 1

HCID 178422430HCID 178422430, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

A mixture of 72 (1.27 g, 6.32 mmol) in formic acid (10 mL) was heated at reflux overnight. The reaction mixture was concentrated in vacuo to afford brown oil, which was treated with a satd. aq. NaHCO3. The aqueous solution was extracted with EtOAc (3×300 mL). The extracts were dried MgSO4), filtered and concentrated to afford 1.09 g (82%) of 5-bromo-7-methyl-1H-benzo[d]imidazole (74) as yellow solid; MS (ESI) m/z 211.1 [M+1]+.

Workup

  1. temperaturewas heated
  2. temperatureat reflux overnight
  3. concentrationThe reaction mixture was concentrated in vacuo
  4. customto afford brown oil, which
  5. additionwas treated with a satd
  6. extractionThe aqueous solution was extracted with EtOAc (3×300 mL)
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-95d2ae4bed634ea7ac6d808a8697db4d
Source dataset
uspto-grants-2014_01
Patent number
US08637537B2

Reaction notes

Loading…