Acetonitrile → HCID 178486135, compound

HRID 250762Notes

Reaction equation

HRID 250762 reaction equation
[OH-].[Na+].C(#N)C.[NH2:6][C:7]1[NH:8][C:9]2[CH:15]=[CH:14][CH:13]=[CH:12][C:10]=2[N:11]=1.[CH3:16][N:17]([CH3:22])[S:18](Cl)(=[O:20])=[O:19]>O>[CH3:16][N:17]([CH3:22])[S:18]([C:12]1[C:10]2[NH:11][C:7]([NH2:6])=[N:8][C:9]=2[CH:15]=[CH:14][CH:13]=1)(=[O:20])=[O:19]

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 136242-AminobenzimidazoleHCID 14798Sodium HydroxideHCID 83372Dimethylsulphamoyl chloride

Product 1

HCID 178486135HCID 178486135, compoundYield 92.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of sodium hydroxide (1.8 g) in water (9 mL) add acetonitrile (44 mL). To this solution, add 2-aminobenzimidazole (3.0 g, 22.5 mmol) and dimethylsulfamoyl chloride (2.4 mL, 22.5 mmol). Stir the reaction mixture at room temperature, overnight. Then, cool the mixture at 0° C. and the product crystallized from solution. Filter the product and dry it in vacuum to provide 5.0 g (90% yield) of the title compound as a white solid. MS (ES+): m/z=241.1 (M+H)+

Workup

  1. customovernight
  2. temperatureThen, cool the mixture at 0° C.
  3. customthe product crystallized from solution
  4. filtrationFilter the product
  5. customdry it in vacuum

Sources & evidence

ORD record
ord-cec107d3b4714c1893b0d352271f0ee2
Source dataset
uspto-grants-2011_01
Patent number
US07863310B2

Reaction notes

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