Triethylamine → 1-(N,N-Dimethylsulfamoyl)-5,6-dimethoxybenzimidazole

HRID 476888Notes

Reaction equation

HRID 476888 reaction equation
[CH3:1][O:2][C:3]1[C:11]([O:12][CH3:13])=[CH:10][C:6]2[N:7]=[CH:8][NH:9][C:5]=2[CH:4]=1.[CH3:14][N:15]([CH3:20])[S:16](Cl)(=[O:18])=[O:17].C(N(CC)CC)C>ClC(Cl)C>[CH3:14][N:15]([CH3:20])[S:16]([N:9]1[C:5]2[CH:4]=[C:3]([O:2][CH3:1])[C:11]([O:12][CH3:13])=[CH:10][C:6]=2[N:7]=[CH:8]1)(=[O:18])=[O:17]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 83372Dimethylsulphamoyl chlorideHCID 6012215,6-Dimethoxybenzimidazole

Product 1

HCID 143713311-(N,N-Dimethylsulfamoyl)-5,6-dimethoxybenzimidazoleYield 86.3%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

A suspension of 5,6-dimethoxybenzimidazole (6.2 g) in dichloroethane (100 ml) was added to N,N-dimethylsulfamoyl chloride (5.3 g) and triethylamine (6 g) was added dropwise while stirring. After the mixture was reacted at room temperature for 24 hours, the reaction solution was washed with an aqueous sodium hydrogen carbonate solution and then with a saturated saline solution and dried over anhydrous Na2SO4. The solvent was distilled off, precipitated crystals were filtered, washed with n-hexane and dried to give the title compound (8.57 g).

Workup

  1. additionwas added dropwise
  2. customAfter the mixture was reacted at room temperature for 24 hours
  3. washthe reaction solution was washed with an aqueous sodium hydrogen carbonate solution
  4. dry with materialwith a saturated saline solution and dried over anhydrous Na2SO4
  5. distillationThe solvent was distilled off
  6. customprecipitated crystals
  7. filtrationwere filtered
  8. washwashed with n-hexane
  9. customdried

Sources & evidence

ORD record
ord-b0c43628ce8748dba12208d09a66786a
Source dataset
uspto-grants-1989_12
Patent number
US04886803

Reaction notes

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