Sodium Chloride → methyl N-{1-[3-(4-methoxyphenyl)phenyl]ethyl}carbamate

HRID 1168033Notes

Reaction equation

HRID 1168033 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:8]([NH:10][C:11](=[O:14])[O:12][CH3:13])[CH3:9])[CH:5]=[CH:6][CH:7]=1.C(=O)([O-])[O-].[Na+].[Na+].[CH3:21][O:22][C:23]1[CH:28]=[CH:27][C:26](OB(O)O)=[CH:25][CH:24]=1.[Cl-].[Na+]>C(O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1(C)C=CC=CC=1>[CH3:21][O:22][C:23]1[CH:28]=[CH:27][C:26]([C:2]2[CH:3]=[C:4]([CH:8]([NH:10][C:11](=[O:14])[O:12][CH3:13])[CH3:9])[CH:5]=[CH:6][CH:7]=2)=[CH:25][CH:24]=1

Participants

8

Reactant 4

HCID 5234Sodium ChlorideHCID 10340Sodium CarbonateHCID 147699944-Methoxyphenyl boric acidHCID 15483792methyl N-[1-(3-bromophenyl)ethyl]carbamate

Product 1

HCID 22995022methyl N-{1-[3-(4-methoxyphenyl)phenyl]ethyl}carbamateYield 144.7%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 1140TolueneSolvent

Procedure

1.00 g of methyl N-[1-(3-bromophenyl)ethyl]carbamate, 0.41 g of sodium carbonate in aqueous solution (20 ml) and 0.09 g of tetrakis(triphenylphosphine)palladium (0) were added to toluene (40 ml) under a nitrogen atmosphere. The resulting solution was mixed with 0.59 g of 4-methoxyphenylboric acid in ethanol (20 ml) at room temperature with stirring and refluxed under heating for 2 hours. After the reaction, the reaction solution was cooled to room temperature, poured into saturated aqueous sodium chloride and extracted with ethyl acetate, and the organic layer was dried over anhydrous magnesium sulfate and evaporated under reduced pressure for removal of the solvent. The residue was purified by silica gel column chromatography to give 1.45 g of methyl N-{1-[3-(4-methoxyphenyl)phenyl]ethyl}carbamate as pale yellow crystals. m.p. 117-119° C.

Workup

  1. temperaturerefluxed
  2. temperatureunder heating for 2 hours
  3. customAfter the reaction
  4. extractionextracted with ethyl acetate
  5. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  6. customevaporated under reduced pressure for removal of the solvent
  7. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-cc1b09f6628d486b98c69a7e9cfed632
Source dataset
uspto-grants-2003_09
Patent number
US06620961B1

Reaction notes

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