Pyridine → Ethyl [1,1'-biphenyl]-2-ylcarbamate

HRID 1351755Notes

Reaction equation

HRID 1351755 reaction equation
Cl[C:2]([O:4][CH2:5][CH3:6])=[O:3].[NH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.N1C=CC=CC=1.[OH-].[Na+]>ClCCl>[CH2:5]([O:4][C:2]([NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)=[O:3])[CH3:6]

Participants

6

Reactant 4

HCID 1049PyridineHCID 70152-AminobiphenylHCID 10928Ethyl chloroformateHCID 14798Sodium Hydroxide

Product 1

HCID 239257Ethyl [1,1'-biphenyl]-2-ylcarbamate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 21.7 g (0.2 mol) of ethyl chloroformate in 20 ml of dichloromethane is slowly added dropwise to a mixture of 25 g of 2-aminobiphenyl (0.148 mol) and 79 g of pyridine (1 mol) in 150 ml of dichloromethane while stirring. After stirring for 12 hours, 100 ml of 10% strength NaOH are added. The aqueous phase is separated off and shaken with dichloromethane. After the dichloromethane extract has been dried over sodium sulfate, the solvent is removed under reduced pressure and the red oil which remains is worked up by column chromatography (silica gel 60, 0.043 . . . 0.060 mm, eluant: hexane/ethyl acetate=9:1). Yield: 31.7 g=89%.

Workup

  1. stirringAfter stirring for 12 hours
  2. customThe aqueous phase is separated off
  3. stirringshaken with dichloromethane
  4. extractionAfter the dichloromethane extract
  5. dry with materialhas been dried over sodium sulfate
  6. customthe solvent is removed under reduced pressure

Sources & evidence

ORD record
ord-14477342b52446fba66c74fe1b91d9db
Source dataset
uspto-grants-2007_05
Patent number
US07217828B2

Reaction notes

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