Water → 1-(3-Chloropropyl)-1,3-dihydro-3-(1-methylvinyl)-2H-benzimidazol-2-one

HRID 911721Notes

Reaction equation

HRID 911721 reaction equation
[H-].[Na+].[C:3]([N:6]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[NH:8][C:7]1=[O:15])([CH3:5])=[CH2:4].[Br:16][CH2:17][CH2:18][CH2:19][Cl:20].O>CN(C=O)C>[Br:16][CH2:17][CH2:18][CH2:19][N:8]1[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[N:6]([C:3]([CH3:5])=[CH2:4])[C:7]1=[O:15].[Cl:20][CH2:19][CH2:18][CH2:17][N:8]1[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[N:6]([C:3]([CH3:5])=[CH2:4])[C:7]1=[O:15]

Participants

7

Reactant 4

HCID 962WaterHCID 80061-Bromo-3-chloropropaneHCID 24758Sodium hydrideHCID 1002781,3-Dihydro-1-(1-methylvinyl)-2H-benzimidazol-2-one

Product 2

HCID 30173591-(3-Chloropropyl)-1,3-dihydro-3-(1-methylvinyl)-2H-benzimidazol-2-oneYield 215%HCID 576565691-(3-BroMopropyl)-1,3-dihydro-3-(1-Methylethenyl)-2H-benziMidazol-2-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Add sodium hydride (600 mg, 16.5 mmol of 60% dispersion in oil) to a solution of 1-isopropenyl-1,3-dihydro-benzoimidazol-2-one (1.311 g, 7.53 mmol) in anhydrous DMF (10 mL) under nitrogen at room temperature and stir for 2 h. Add 1-bromo-3-chloropropane (900 μL, 9.03 mmol) and stir for 3 days. Pour the suspension into water (100 mL), extract with diethyl ether (2×50 mL). Wash the organic extract with brine (100 mL), dry over MgSO4 and concentrate in vacuo to give the title compound impurified with 1-(3-chloro-propyl)-3-isopropenyl-1,3-dihydro-benzoimidazol-2-one (2.03 g, 1:1 mixture). MS (ES+) m/z: 251 (M+H)+, 293 (M+H)+.

Workup

  1. extractionextract with diethyl ether (2×50 mL)
  2. washWash the
  3. extractionorganic extract with brine (100 mL)
  4. dry with materialdry over MgSO4
  5. concentrationconcentrate in vacuo

Sources & evidence

ORD record
ord-66e7a7c7cedb44d390ced262434815e0
Source dataset
uspto-grants-2011_09
Patent number
US08022062B2

Reaction notes

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