Hydrochloric Acid → HCID 11035364, compound

HRID 273935Notes

Reaction equation

HRID 273935 reaction equation
[C:1]1([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:6]=[CH:5][C:4]([O:7][CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[C:15](=[O:20])[C:16](OC)=[O:17])=[CH:3][CH:2]=1.C1COCC1.[CH3:32][NH2:33].Cl>CO.O>[CH3:32][NH:33][C:16](=[O:17])[C:15]([C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=1[CH2:8][O:7][C:4]1[CH:5]=[CH:6][C:1]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[CH:2][CH:3]=1)=[O:20]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6329MethylamineHCID 8028TetrahydrofuranHCID 21470369HCID 21470369, compound

Product 1

HCID 11035364HCID 11035364, compoundYield 81.9%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 962WaterSolvent

Procedure

To methyl 2-[2-(biphenyl-4-yloxymethyl)phenyl]-2-oxoacetate (3.46 g, 0.01 mol), added were anhydrous methanol (10 ml), dry THF (10 ml) and a 40% solution (2.33 g) of methyl amine (0.03 mol) in methanol, and the reaction mixture was stirred at room temperature for 2 hour. After completion of the reaction, water (150 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 (150 ml). The extract was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The obtained crystals (3.42 g; yield, 99.1%) were recrystallized from ethyl acetate/n-hexane to give N-methyl-2-[2-(biphenyl-4-yloxymethyl)phenyl] -2-oxoacetamide (2.83 g) as colorless crystals (m.p.: 144°-145° C.).

Workup

  1. additionwas added to the reaction mixture which
  2. extractionextracted with ethyl acetate (150 ml)
  3. dry with materialThe extract was dried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe obtained crystals (3.42 g; yield, 99.1%)
  6. customwere recrystallized from ethyl acetate/n-hexane

Sources & evidence

ORD record
ord-603a6ac451e64dc8876549dd061593de
Source dataset
uspto-grants-1995_02
Patent number
US05387714

Reaction notes

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