2,6-Lutidine → Benzyl carbamate

HRID 2070035Notes

Reaction equation

HRID 2070035 reaction equation
OCCC1C=CC([NH2:8])=CC=1C(F)(F)F.N1C(C)=CC=CC=1C.Cl[C:24]([O:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=[O:25]>C(Cl)Cl>[CH2:27]([O:26][C:24](=[O:25])[NH2:8])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

5

Reactant 3

HCID 79372,6-LutidineHCID 10387Benzyl chloroformateHCID 231551264-(2-Hydroxyethyl)-3-(trifluoromethyl)aniline

Product 1

HCID 12136Benzyl carbamateYield 141.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-(2-Hydroxyethyl)-3-(trifluoromethyl)aniline (408 mg, 2.0 mmol) was dissolved in DCM (10 mL), and 2,6-lutidine (426 mg, 4.0 mmol) and then benzyl chloroformate (678 mg, 4.0 mmol) were dropwise added thereto. The resulting mixture was stirred at room temperature for 1.5 hours. The reaction solution was quenched with a saturated sodium bicarbonate solution, and the organic layer was washed with saturated brine and concentrated under reduced pressure. The residue was purified by silica-gel column chromatography (n-hexane:ethyl acetate=3:1) to give 4-(2-hydroxyethyl)-3-(trifluoromethyl)phenyl]carbamic acid benzyl ester (429 mg, 64%) as a light-yellow oil.

Workup

  1. customThe reaction solution was quenched with a saturated sodium bicarbonate solution
  2. washthe organic layer was washed with saturated brine
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by silica-gel column chromatography (n-hexane:ethyl acetate=3:1)

Sources & evidence

ORD record
ord-175eb8b1741e4063b7d63fc8190382d8
Source dataset
uspto-grants-2012_10
Patent number
US08299252B2

Reaction notes

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