Dimethylformamide → 1-(Methylsulfonyl)-1H-Benzimidazol-2-Amine

HRID 29147

Reaction equation

HRID 29147 reaction equation
[NH2:1][C:2]1[NH:3][C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=1.CN(C=O)C.[CH3:16][S:17](Cl)(=[O:19])=[O:18]>C(Cl)Cl>[CH3:16][S:17]([N:3]1[C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=[C:2]1[NH2:1])(=[O:19])=[O:18]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 136242-AminobenzimidazoleHCID 31297Methanesulfonyl chloride

Product 1

HCID 229970451-(Methylsulfonyl)-1H-Benzimidazol-2-AmineYield 28.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-amino-benzimidazole (1.0 g, 7.5 mmol) was dissolved in 15 mL of anhydrous CH2Cl2 and 3 mL anhydrous DMF and cooled to ˜0° C. Trethylamine (1.6 mL, 1.5 eq.) was added followed by an addition of methanesulfonylchloride (580 μL, 7.5 mmol) over ˜1 minute. After 1 minute at ˜0° C., the reaction was warmed to RT. After 1 hour the reaction was quenched with water, and partitioned between a saturated sodium bicarbonate solution and CH2Cl2. The aqueous layer was extracted with CH2Cl2 and the combined organic layers were washed with water (2 times), brine then dried over NaSO4, filtered and the solvent was removed in vacuo to give 455 mg of N-methanesulfonyl-2-aminobenzimidazole. HPLC shows the material to be 91% pure, (ret. time=3.70). LCMS: obs. M+H@ 212.1 amu. The material was carried on without purification.

Workup

  1. additionTrethylamine (1.6 mL, 1.5 eq.) was added
  2. customAfter 1 hour the reaction was quenched with water
  3. custompartitioned between a saturated sodium bicarbonate solution and CH2Cl2
  4. extractionThe aqueous layer was extracted with CH2Cl2
  5. washthe combined organic layers were washed with water (2 times), brine
  6. dry with materialthen dried over NaSO4
  7. filtrationfiltered
  8. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-457a04e2ceaa47618209d9626c06d3bb
Source dataset
uspto-grants-2008_09
Patent number
US07419967B2

Linked notes

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