Chloroform → HCID 19978316, compound

HRID 1449493Notes

Reaction equation

HRID 1449493 reaction equation
[C:1]([N:9]1[CH:13]2[CH2:14][CH2:15][CH2:16][CH2:17][CH:12]2[NH:11][C:10]1=[O:18])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[Br:21][CH2:22][CH2:23][CH2:24][CH2:25]Br.C(Cl)(Cl)Cl>CN(C)C=O>[C:1]([N:9]1[CH:13]2[CH2:14][CH2:15][CH2:16][CH2:17][CH:12]2[N:11]([CH2:25][CH2:24][CH2:23][CH2:22][Br:21])[C:10]1=[O:18])(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 6212ChloroformHCID 80561,4-DibromobutaneHCID 24758Sodium hydrideHCID 19978293HCID 19978293, compound

Product 1

HCID 19978316HCID 19978316, compoundYield 39.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 3-benzoylperhydrobenzimidazol-2-one (2.7 9, 10.0 mmoles) in 50 ml of dimethylformamide was added 60% sodium hydride (400 mg, 10.0 mmoles), and the mixture was stirred at 60° C. for 30 minutes. To this mixture having been cooled to room temperature was further added 1,4-dibromobutane (10.8 g, 50.0 mmoles), and the resulting mixture was stirred at 60° C. for 4 hours. After chloroform was added to the reaction, insolubles were removed by filtration, the filtrate was washed with water, and the solvent was evaporated. The residue thus obtained was purified by chromatography on a silica gel column to give 1.5 g of the title compound as an oil.

Workup

  1. temperatureTo this mixture having been cooled to room temperature
  2. stirringthe resulting mixture was stirred at 60° C. for 4 hours
  3. customwere removed by filtration
  4. washthe filtrate was washed with water
  5. customthe solvent was evaporated
  6. customThe residue thus obtained
  7. customwas purified by chromatography on a silica gel column

Sources & evidence

ORD record
ord-d31c8c66adb645948aecd56db38aa7a8
Source dataset
uspto-grants-1997_02
Patent number
US05599815

Reaction notes

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