Ammonia → HCID 22291402, compound

HRID 967812Notes

Reaction equation

HRID 967812 reaction equation
[C:1]1([C:7]2[N:8]=[CH:9][NH:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[CH:13]([OH:21])[CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C([O-])([O-])=O.[Na+].[Na+].N>CN1CCN(C)C1=O>[C:1]1([C:7]2[N:8]=[CH:9][N:10]([C:18]3[CH:19]=[CH:20][C:15]([CH2:14][CH2:13][OH:21])=[CH:16][CH:17]=3)[CH:11]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 222AmmoniaHCID 10340Sodium CarbonateHCID 17845791HCID 17845791, compoundHCID 178418822HCID 178418822, compound

Product 1

HCID 22291402HCID 22291402, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 66611,3-Dimethyl-2-imidazolidinoneSolvent

Conditions

Temperature
180 °C

Procedure

A mixture of 4-phenylimidazole (4.32 g, 30 mmol), Bromophenethyl alcohol (10.5 ml, 75 mmol), CuBr (10.4 g, 72 mmol) and Na2CO3 (3.8 g, 36 mmol) in 1,3-dimethyl-2-imidazolidinone (100 mL) was stirred at 180° C. for 36 h. After cooling, to the mixture was added 25% NH3 aq. (50 mL). After 30 min, insoluble materials were removed by Celite filtration and washed with dichloromethane. The aqueous layer was extracted with dichloromethane. The organic phase was dried (MgSO4) and concentrated under reduced pressure. To the residue was added diisopropylether (100 mL) and the flask was cooled to 0° C. Filtration of the diisopropylether gave 4.01 g of the title compound as colorless solid (51%): MS (ESI) m/z 265 [M+H]+, 1H-NMR (CDCl3) δ 2.94 (2H, t, J=6.4 Hz), 3.93 (2H, br), 7.26-7.30 (2H, m), 7.35-7.44 (5H, m), 7.55 (1H, d, J=1.2 Hz), 7.82-7.86 (3H, m).

Workup

  1. temperatureAfter cooling, to the mixture
  2. waitAfter 30 min
  3. custominsoluble materials were removed by Celite filtration
  4. washwashed with dichloromethane
  5. extractionThe aqueous layer was extracted with dichloromethane
  6. dry with materialThe organic phase was dried (MgSO4)
  7. concentrationconcentrated under reduced pressure
  8. additionTo the residue was added diisopropylether (100 mL)
  9. temperaturethe flask was cooled to 0° C
  10. filtrationFiltration of the diisopropylether

Sources & evidence

ORD record
ord-c4b662a8abe346eb959cb567c132e862
Source dataset
uspto-grants-2005_10
Patent number
US06956050B2

Reaction notes

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