Sodium hydride → HCID 59075602, compound

HRID 1355489Notes

Reaction equation

HRID 1355489 reaction equation
[CH3:1][N:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[NH:4][C:3]1=[O:11].[H-].[Na+].[Cl:14][CH2:15]/[CH:16]=[CH:17]\[CH2:18]Cl>CN(C=O)C>[Cl:14][CH2:15]/[CH:16]=[CH:17]\[CH2:18][N:4]1[C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=2[N:2]([CH3:1])[C:3]1=[O:11]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 5905401-methyl-2,3-dihydro-1H-1,3-benzodiazol-2-oneHCID 64321151,4-Dichloro-cis-2-butene

Product 1

HCID 59075602HCID 59075602, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Conditions

Temperature
40 °C

Procedure

A solution of 1-methyl-1,3-dihydro-2H-benzimidazol-2-one (2 g, 13 mmoles) in DMF (50 ml) was added dropwise and at room temperature to a suspension of 80% sodium hydride (0.4 g, 13 mmoles) in DMF (25 ml). The mixture was heated at 40° C. for 30 minutes and cis-1,4-dichloro-2-butene (2.84 ml, 27 mmoles) in DMF (30 ml) was dropped in 4 hours under stirring. After stirring overnight at room temperature, the reaction mixture was poured into ice water and extracted with ethyl acetate. The organic layer was evaporated and the crude residue was purified by flash chromatography (hexane-ethyl acetate 55-45) to give 1.4 of the title compound as a thick yellowish oil.

Workup

  1. stirringAfter stirring overnight at room temperature
  2. extractionextracted with ethyl acetate
  3. customThe organic layer was evaporated
  4. customthe crude residue was purified by flash chromatography (hexane-ethyl acetate 55-45)

Sources & evidence

ORD record
ord-a9597ef213b948448daaebc9b2fb03e8
Source dataset
uspto-grants-2003_07
Patent number
US06586435B2

Reaction notes

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