Benzyl chloroformate → HCID 57663980, compound

HRID 1510244Notes

Reaction equation

HRID 1510244 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([C:7]2[CH:13]=[CH:12][C:10]([NH2:11])=[CH:9][CH:8]=2)=[CH:3][CH:2]=1.[CH2:14]([O:21][C:22](Cl)=[O:23])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>ClCCl.N1C=CC=CC=1>[N:1]1[CH:6]=[CH:5][C:4]([C:7]2[CH:13]=[CH:12][C:10]([NH:11][C:22](=[O:23])[O:21][CH2:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[CH:9][CH:8]=2)=[CH:3][CH:2]=1

Participants

5

Reactant 2

HCID 10387Benzyl chloroformateHCID 15126544-(Pyridin-4-yl)aniline

Product 1

HCID 57663980HCID 57663980, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

To a suspension of 4-(4-pyridinyl)aniline (50 mg) in dichloromethane (1.50 mL) and pyridine (356.4 μL) was added dropwise benzyloxycarbonyl chloride (75.5 μL) at ambient temperature and the mixture was stirred at the same temperature for 1 hour. The resulting mixture was concentrated in vacuo and water (10 mL) was added to the residue. The aqueous solution was extracted with ethyl acetate (15 mL) and the organic layer was washed successively with saturated sodium bicarbonate aqueous solution and brine, then dried and concentrated. The residual solid was triturated with diisopropylether (2.0 mL) to give benzyl [4-(4-pyridinyl)phenyl]carbamate (70.3 mg) as a yellow solid.

Workup

  1. concentrationThe resulting mixture was concentrated in vacuo and water (10 mL)
  2. additionwas added to the residue
  3. extractionThe aqueous solution was extracted with ethyl acetate (15 mL)
  4. washthe organic layer was washed successively with saturated sodium bicarbonate aqueous solution and brine
  5. customdried
  6. concentrationconcentrated
  7. customThe residual solid was triturated with diisopropylether (2.0 mL)

Sources & evidence

ORD record
ord-852e77a2d0d24945ac236ea5a6dda3cf
Source dataset
uspto-grants-2012_07
Patent number
US08211919B2

Reaction notes

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