Dimethyl Sulfate → 2,2'-Bi-1H-benzimidazole, 1-methyl-

HRID 1471229Notes

Reaction equation

HRID 1471229 reaction equation
[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]1[NH:14][C:13]2[CH:15]=[CH:16][CH:17]=[CH:18][C:12]=2[N:11]=1.[OH-].[Na+].[CH3:21]OS(OC)(=O)=O>CN(C)C=O>[CH3:21][N:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]1[NH:11][C:12]2[CH:18]=[CH:17][CH:16]=[CH:15][C:13]=2[N:14]=1

Participants

5

Reactant 3

HCID 6497Dimethyl Sulfate3×HCID 14798Sodium Hydroxide2×HCID 2490972,2'-Bi-1H-benzimidazole

Product 1

HCID 40438612,2'-Bi-1H-benzimidazole, 1-methyl-Yield 39.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a flask were added 1.2 g 1H,1′H-2,2′-bibenzimidazole, 0.45 g sodium hydroxide, 100 ml N,N-dimethylformamide and 1.4 g dimethylsulfate. The mixture was heated to 45 C under nitrogen for 16 hours and another 0.45 g sodium hydroxide and 2.8 g dimethylsulfate were added and the mixture was stirred at 45 C for 24 hours. Another 4.2 g of dimethylsulfate were added and the mixture was stirred at 45 C for 24 hours, then cooled to 22 C and quenched with 350 ml water. The off-white solid was filtered and washed with water. After dissolving the product in 125 ml hot ethanol, 44 ml water were added and the solution was cooled to 5 C, filtered, washed with 50% ethanol and dried leaving 0.5 g white solid.

Workup

  1. temperatureThe mixture was heated to 45 C under nitrogen for 16 hours
  2. stirringthe mixture was stirred at 45 C for 24 hours
  3. temperaturecooled to 22 C
  4. customquenched with 350 ml water
  5. filtrationThe off-white solid was filtered
  6. washwashed with water
  7. dissolutionAfter dissolving the product in 125 ml hot ethanol
  8. addition44 ml water were added
  9. temperaturethe solution was cooled to 5 C
  10. filtrationfiltered
  11. washwashed with 50% ethanol
  12. customdried

Sources & evidence

ORD record
ord-d0b5463f9f2a42f981e29190b8016471
Source dataset
uspto-grants-2015_04
Patent number
US09011734B2

Reaction notes

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