Triethylamine → N-[2-(2-oxo-2,3-dihydro-1H-benzimidazol-1-yl)ethyl]methanesulfonamide

HRID 1059651Notes

Reaction equation

HRID 1059651 reaction equation
Cl.[NH2:2][CH2:3][CH2:4][N:5]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[NH:7][C:6]1=[O:14].C(N(CC)CC)C.[CH3:22][S:23](Cl)(=[O:25])=[O:24]>C1COCC1>[O:14]=[C:6]1[N:5]([CH2:4][CH2:3][NH:2][S:23]([CH3:22])(=[O:25])=[O:24])[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[NH:7]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 186308891-(2-aminoethyl)-2,3-dihydro-1H-1,3-benzodiazol-2-one hydrochloride

Product 1

HCID 18630866N-[2-(2-oxo-2,3-dihydro-1H-benzimidazol-1-yl)ethyl]methanesulfonamideYield 15.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-(2-aminoethyl)-1,3-dihydro-2H-benzimidazol-2-one hydrochloride (2.8 g, 13 mmoles) in THF (30 ml) and triethyl amine (5.5 ml, 39 mmoles) was added methanesulfonyl chloride (1.12 ml, 14 mmoles) and the reaction mixture was stirred for 2 hours at room temperature. The organic solvent was evaporated and the residue was partitioned into water and ethyl acetate. The organic layer was washed with saturated aqueous Na2CO3 solution and taken to dryness. The crude residue was purified by flash chromatography (CH2Cl2-methanol 96-4) to give 0.5 g of the title compound as a white solid. M.p. 162-170° C.

Workup

  1. customThe organic solvent was evaporated
  2. customthe residue was partitioned into water and ethyl acetate
  3. washThe organic layer was washed with saturated aqueous Na2CO3 solution
  4. customThe crude residue was purified by flash chromatography (CH2Cl2-methanol 96-4)

Sources & evidence

ORD record
ord-8d358ff621344339aee6be9fe820a88f
Source dataset
uspto-grants-2003_02
Patent number
US06521623B1

Reaction notes

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