Water → HCID 70234718, compound

HRID 651377Notes

Reaction equation

HRID 651377 reaction equation
[CH2:1]([O:3][C:4]([N:6]1[C:10]2[CH:11]=[CH:12][C:13]([O:15][CH3:16])=[CH:14][C:9]=2[NH:8][C:7]1=[O:17])=[O:5])[CH3:2].[H-].[Na+].Br[CH2:21][CH2:22][Cl:23].O>CN(C=O)C>[CH2:1]([O:3][C:4]([N:6]1[C:10]2[CH:11]=[CH:12][C:13]([O:15][CH3:16])=[CH:14][C:9]=2[N:8]([CH2:21][CH2:22][Cl:23])[C:7]1=[O:17])=[O:5])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 78491-Bromo-2-ChloroethaneHCID 24758Sodium hydrideHCID 70127753HCID 70127753, compound

Product 1

HCID 70234718HCID 70234718, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 5-methoxy-2-oxo-2,3-dihydrobenzimidazole-1-carboxylic acid ethyl ester and 80% NaH (0.38 g; 0.013 mol) in anhydrous DMF was stirred 20 minutes at room temperature. Then 1-bromo-2-chloroethane (1.1 ml; 0.013 moles) was added and the solution was stirred overnight. After cooling, the reaction mixture was poured into water and the separated oil was extracted into ethyl acetate. The organic layer was dried over MgSO4 and evaporated under vacuum to give the crude title compound which was crystallized with diisopropyl ether. White solid. 1.35 g; m.p. 116-118° C.

Workup

  1. stirringthe solution was stirred overnight
  2. temperatureAfter cooling
  3. extractionthe separated oil was extracted into ethyl acetate
  4. dry with materialThe organic layer was dried over MgSO4
  5. customevaporated under vacuum

Sources & evidence

ORD record
ord-b6d900ad0d4a477db534fe12ab38397f
Source dataset
uspto-grants-2001_08
Patent number
US06281218B1

Reaction notes

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