Hydrochloric Acid → HCID 11035364, compound

HRID 273925Notes

Reaction equation

HRID 273925 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][O:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:12][CH:11]=1.[Mg].BrC(Br)C.[C:27](Cl)(=[O:31])[C:28](Cl)=[O:29].[CH3:33][NH2:34].Cl>C1COCC1.CO.O>[CH3:33][NH:34][C:27](=[O:31])[C:28]([C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][O:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:12][CH:11]=1)=[O:29]

Participants

10

Reactant 6

HCID 313Hydrochloric AcidHCID 6329MethylamineHCID 112011,1-DibromoethaneHCID 65578Oxalyl chlorideHCID 5462224MagnesiumHCID 15239354HCID 15239354, compound

Product 1

HCID 11035364HCID 11035364, compoundYield 71%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent4×

Conditions

Temperature
65 °C

Procedure

In a stream of argon gas, 1-bromo-2-(biphenyl-4-yloxymethyl)benzene (33.92 g, 0.1 mol) in dry THF (140 ml) was dropwise added to a mixture of magnesium (4.86 g, 0.2 mol) and dibromoethane (0.2 ml) in dry THF (20 ml) at 50° to 60° C. over 40 minutes. The reaction mixture was stirred at 65° C. for 1 hour, diluted with dry THF (90 ml) and cooled below 20° C. This mixture was dropwise added to a solution of oxalyl chloride (15.23 g, 0.12 mol) in dry THF (250 ml) at -50° C. over 15 minutes, followed by stirring at -75° C. for 1 hour, and a 40% solution (46.59 g) of methylamine (0.6 mol) in methanol was added thereto at -20° C., followed by stirring at room temperature for 1 hour. After completion of the reaction, water (1000 ml) was added to the reaction mixture which was then adjusted to below pH 2 by addition of conc. HCl and extracted with ethyl acetate (600 ml). The extract was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel chromatography (ethyl acetate/n-hexane) to give N-methyl-2-[2-(biphenyl-4-yloxymethyl)phenyl]-2-oxoacetamide (24.52 g; yield, 71.0%) as colorless crystals.

Workup

  1. temperaturecooled below 20° C
  2. stirringby stirring at -75° C. for 1 hour
  3. customat -20° C.
  4. stirringby stirring at room temperature for 1 hour
  5. additionwas added to the reaction mixture which
  6. extractionextracted with ethyl acetate (600 ml)
  7. dry with materialThe extract was dried over anhydrous magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by silica gel chromatography (ethyl acetate/n-hexane)

Sources & evidence

ORD record
ord-cd959b4d2fa8415a832cee510e1b4966
Source dataset
uspto-grants-1995_02
Patent number
US05387714

Reaction notes

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