N,N-Dimethylglycine → HCID 118114109, compound

HRID 1509651Notes

Reaction equation

HRID 1509651 reaction equation
Br[C:2]1[CH:7]=[C:6]([C:8]([CH3:11])([CH3:10])[CH3:9])[CH:5]=[C:4]([Br:12])[CH:3]=1.[NH:13]1[CH:17]=[CH:16][N:15]=[CH:14]1.C([O-])([O-])=O.[K+].[K+].CN(C)CC(O)=O>CS(C)=O.C(OCC)(=O)C.[Cu]I>[Br:12][C:4]1[CH:3]=[C:2]([N:13]2[CH:17]=[CH:16][N:15]=[CH:14]2)[CH:7]=[C:6]([C:8]([CH3:11])([CH3:10])[CH3:9])[CH:5]=1

Participants

8

Reactant 4

HCID 673N,N-DimethylglycineHCID 795ImidazoleHCID 11430Potassium CarbonateHCID 27611701,3-dibromo-5-tert-butylbenzene

Product 1

HCID 118114109HCID 118114109, compound

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 1,3-dibromo-5-tert-butylbenzene (2.92 g, 10.0 mmol, 1.0 eq), 1H-imidazole (0.69 g, 10.0 mmol, 1.0 eq), CuI (0.19 g, 1.0 mmol, 0.10 eq), K2CO3 (2.76 g, 20.0 mmol, 2.0 eq) and 2-(dimethylamino)acetic acid (0.21 g, 2.0 mmol, 0.20 eq) in DMSO (10 mL) was stirred at a temperature of 110° C. for four days under a nitrogen atmosphere, then cooled down to ambient temperature. The mixture was diluted with plenty of ethyl acetate and filtered. The filtrate was washed with water three times, dried over sodium sulfate, then filtered, and the filtrate was concentrated under reduced pressure. The residue was purified through column chromatography on silica gel using hexane and ethyl acetate as an eluent to obtain the desired product, 1-(3-bromo-5-tert-butylphenyl)-1H-imidazole 7, as a brown sticky liquid (1.56 g in 56% yield).

Workup

  1. temperaturecooled down to ambient temperature
  2. filtrationfiltered
  3. washThe filtrate was washed with water three times
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. customThe residue was purified through column chromatography on silica gel

Sources & evidence

ORD record
ord-26c0243dd5c143d58666e829b57b7d8e
Source dataset
uspto-grants-2015_12
Patent number
US09224963B2

Reaction notes

Loading…