Hydrochloric Acid → N-[2-(2-oxo-2,3-dihydro-1H-benzimidazol-1-yl)ethyl]-acetamide

HRID 1059650Notes

Reaction equation

HRID 1059650 reaction equation
[OH-].[Na+].Cl.[NH2:4][CH2:5][CH2:6][N:7]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[NH:9][C:8]1=[O:16].[C:17](OC(=O)C)(=[O:19])[CH3:18].Cl>O.O1CCOCC1>[O:16]=[C:8]1[N:7]([CH2:6][CH2:5][NH:4][C:17](=[O:19])[CH3:18])[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[NH:9]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 7918Acetic AnhydrideHCID 14798Sodium HydroxideHCID 186308891-(2-aminoethyl)-2,3-dihydro-1H-1,3-benzodiazol-2-one hydrochloride

Product 1

HCID 18630881N-[2-(2-oxo-2,3-dihydro-1H-benzimidazol-1-yl)ethyl]-acetamide

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 312751,4-DioxaneSolvent

Procedure

To a cooled solution of NaOH (0.41 g, 10 mmoles) in water (5 ml) were simultaneously added 1-(2-aminoethyl)-1,3-dihydro-2H-benzimidazol-2-one hydrochloride (0.7 g, 3.3 mmoles) and a solution of acetic anhydride (0.37 ml, 3.9 mmoles) in dioxane (10 ml). The reaction mixture was stirred for 2 hours at room temperature and then taken to dryness. The residue was dissolved in water, adjusted to pH 4 with 10% aqueous HCl, and extracted with CHCl3. The organic layer was taken to dryness and from the crude residue 0.35 g of the title compound was obtained after crystallization from diethyl ether. M.p. 153° C.

Workup

  1. extractionextracted with CHCl3
  2. customwas obtained
  3. customafter crystallization from diethyl ether

Sources & evidence

ORD record
ord-a38627d3beb243febf0f05de6de033d3
Source dataset
uspto-grants-2003_02
Patent number
US06521623B1

Reaction notes

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