Hydrochloric Acid → (1,2-dimethyl-1H-imidazol-5-yl)(phenyl)methanone

HRID 875215Notes

Reaction equation

HRID 875215 reaction equation
Br[C:2]1[N:6]([CH3:7])[C:5]([CH3:8])=[N:4][CH:3]=1.C([Mg]Br)C.CON(C)[C:16](=[O:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.Cl>ClCCl.O>[CH3:7][N:6]1[C:2]([C:16]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[O:23])=[CH:3][N:4]=[C:5]1[CH3:8]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 569575N-Methoxy-N-methylbenzamideHCID 72048795-bromo-1,2-dimethyl-1H-imidazoleHCID 178418443HCID 178418443, compound

Product 1

HCID 66887800(1,2-dimethyl-1H-imidazol-5-yl)(phenyl)methanoneYield 73.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-bromo-1,2-dimethyl-1H-imidazole (10.0 g, 57.1 mmol) in dichloromethane (50 mL) was added dropwise ethylmagnesium bromide (3 M in Et2O, 19.0 mL, 57.0 mmol). After stirring at room temperature for 30 min, the reaction mixture was cooled down to 0° C. with an ice-brine bath and N-Methoxy-N-methyl-benzamide (8.70 mL, 57.1 mmol) was added dropwise. The mixture was stirred for 7.5 h at room temperature. The mixture was worked-up by addition of water (100 mL), then acidified with aq. HCl (1 M) until pH=7. After extraction with dichloromethane (2×75 mL), the organic layers were washed with water (2×100 mL) then dried over MgSO4 and concentrated in vacuo. Purification of the residue on silica gel afforded (1,2-dimethyl-1H-imidazol-5-yl)(phenyl)methanone [8.41 g, yield 44%; HPLC/MS: m/z=201 (M+H); log P(HCOOH)=0.56].

Workup

  1. temperaturethe reaction mixture was cooled down to 0° C. with an ice-brine bath
  2. stirringThe mixture was stirred for 7.5 h at room temperature
  3. extractionAfter extraction with dichloromethane (2×75 mL)
  4. washthe organic layers were washed with water (2×100 mL)
  5. dry with materialthen dried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customPurification of the residue on silica gel

Sources & evidence

ORD record
ord-c5a3ad3b321443889f351ad04f80e039
Source dataset
uspto-grants-2015_03
Patent number
US08981111B2

Reaction notes

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