Water → HCID 69972959, compound

HRID 1059653Notes

Reaction equation

HRID 1059653 reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][CH2:8][CH2:9][N:10]1[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[NH:12][C:11]1=[O:19].[H-].[Na+].[Cl:22][CH2:23]/[CH:24]=[CH:25]\[CH2:26]Cl.O>CN(C=O)C>[Cl:22][CH2:23]/[CH:24]=[CH:25]\[CH2:26][N:12]1[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[N:10]([CH2:9][CH2:8][O:7][CH:2]2[CH2:3][CH2:4][CH2:5][CH2:6][O:1]2)[C:11]1=[O:19]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 64321151,4-Dichloro-cis-2-buteneHCID 18630869HCID 18630869, compound

Product 1

HCID 69972959HCID 69972959, compoundYield 17.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1-[2-(tetrahydro-2H-pyran-2yloxy)ethyl]-1,3-dihydro-2H-benzimidazol-2-one (12 g, 46 mmoles) in DMF (120 ml) was added 80% sodium hydride (1.7 g, 55 mmoles) and the mixture was stirred at room temperature for 1 hour. Cis-1,4-dichloro-2-butene (5.8 ml, 55 mmoles) was added dropwise and the reaction mixture was stirred for 3 hours at room temperature. The reaction mixture was poured into water and extracted with ethyl acetate. The organic layer was taken to dryness and the residue was purified by flash chromatography (cyclohexane-ethyl acetate 70-30) to give 2.8 g of the title compound as a thick oil which was used without any further purification.

Workup

  1. stirringthe reaction mixture was stirred for 3 hours at room temperature
  2. extractionextracted with ethyl acetate
  3. customthe residue was purified by flash chromatography (cyclohexane-ethyl acetate 70-30)

Sources & evidence

ORD record
ord-07d4fff3ea52446b8501e1fe33051099
Source dataset
uspto-grants-2003_02
Patent number
US06521623B1

Reaction notes

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