1,3-Dibromopropane → HCID 57656420, compound

HRID 911720Notes

Reaction equation

HRID 911720 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+].[Br:14][CH2:15][CH2:16][CH2:17]Br>C1COCC1.[Cl-].[Na+].O>[Br:14][CH2:15][CH2:16][CH2:17][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

6

Reactant 3

HCID 80011,3-DibromopropaneHCID 24758Sodium hydrideHCID 5905401-methyl-2,3-dihydro-1H-1,3-benzodiazol-2-one

Product 1

HCID 57656420HCID 57656420, compoundYield 30%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

Add portion wise 3-methyl-1,3-dihydro-benzoimidazol-2-one (400 mg, 27.0 mmol) to a suspension of sodium hydride (1.296 g, 32.4 mmol of 60% dispersion in oil) in anhydrous THF (200 mL) under nitrogen over 15 min, then continue to stir for 30 min. Add 1,3-dibromopropane (11.0 mL, 108 mmol) and stir overnight. Then heat at reflux for 3 days. Cool the suspension to room temperature, pour into brine (400 mL), extract with diethyl ether (300 mL), dry over MgSO4 and concentrate in vacuo. Purify by chromatography on silica gel eluting with isohexane/EtOAc (1:0 to 1:1 gradient over 40 min) to give the title compound as a colourless oil (2.15 g, 30%).

Workup

  1. temperatureThen heat
  2. temperatureat reflux for 3 days
  3. extractionextract with diethyl ether (300 mL)
  4. dry with materialdry over MgSO4
  5. concentrationconcentrate in vacuo
  6. customPurify by chromatography on silica gel eluting with isohexane/EtOAc (1:0 to 1:1 gradient over 40 min)

Sources & evidence

ORD record
ord-6b543913a66c4c008cd56b96a95c4ced
Source dataset
uspto-grants-2011_09
Patent number
US08022062B2

Reaction notes

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