Methyl chloroformate → HCID 71227062, compound

HRID 2409917Notes

Reaction equation

HRID 2409917 reaction equation
Cl[C:2]([O:4][CH3:5])=[O:3].[O:6]1[C:10]([C:11]2[CH:12]=[C:13]([CH:15]=[CH:16][CH:17]=2)[NH2:14])=[CH:9][N:8]=[CH:7]1>C1COCC1>[O:6]1[C:10]([C:11]2[CH:12]=[C:13]([NH:14][C:2](=[O:3])[O:4][CH3:5])[CH:15]=[CH:16][CH:17]=2)=[CH:9][N:8]=[CH:7]1

Participants

4

Reactant 2

HCID 6586Methyl chloroformateHCID 27392893-(1,3-Oxazol-5-yl)aniline

Product 1

HCID 71227062HCID 71227062, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methyl chloroformate (1.67 mL, 21.54 mmol) was slowly added to a 0° C. solution of 3-(oxazol-5-yl)aniline (2.30 gm, 14.36 mmol) and TEA (4.00 mL, 28.70 mmol) in THF (65 mL). The ice bath was removed and the reaction mixture was stirred at rt. After 2.5 h the reaction mixture was concentrated and the residue was partitioned between EtOAc and water. The organic phase was isolated, washed with 1 N HCl (2×) and saturated aqueous NaCl, dried over MgSO4, filtered and concentrated. The resulting residue was purified using silica gel chromatography eluting with a gradient of 0-100% EtOAc/Hexanes to give the product, methyl 3-(oxazol-5-yl)phenylcarbamate, (1.34 gm, 6.14 mmol, 43% yield) as a white solid. Anal. Calcd. for C11H10N2O3 m/z 218.1, found: 219.1 (M+H)+.

Workup

  1. customThe ice bath was removed
  2. concentrationAfter 2.5 h the reaction mixture was concentrated
  3. customthe residue was partitioned between EtOAc and water
  4. customThe organic phase was isolated
  5. washwashed with 1 N HCl (2×) and saturated aqueous NaCl
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe resulting residue was purified
  10. washeluting with a gradient of 0-100% EtOAc/Hexanes

Sources & evidence

ORD record
ord-e985cac8a5ed4633bcbd05ec1b44ecc7
Source dataset
uspto-grants-2014_08
Patent number
US08815909B2

Reaction notes

Loading…