Epichlorohydrin → 4-Oxiranylmethoxy-benzamide

HRID 750752Notes

Reaction equation

HRID 750752 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH2:8])=[O:7])=[CH:4][CH:3]=1.[CH2:11]([CH:13]1[O:15][CH2:14]1)Cl.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[O:15]1[CH2:14][CH:13]1[CH2:11][O:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH2:8])=[O:7])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 7835EpichlorohydrinHCID 11430Potassium CarbonateHCID 650524-Hydroxybenzamide

Product 1

HCID 122382474-Oxiranylmethoxy-benzamideYield 28.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

To a sealed tube was added 4-hydroxybenzamide (200 mg, 1.458 mmol), epichlorohydrin (135 mg, 1.458 mmol) and potassium carbonate (403 mg, 2.916 mmol) in 7 mL of dry DMF. The reaction mixture was stirred at 70° C. for 18 h. The reaction mixture was filtered and concentrated. The residue was purified by flash chromatography, eluting with 0-5% 2M NH3 in MeOH/CH2Cl2. The product fractions were collected and concentrated to afford 80 mg of 4-oxiranylmethoxy-benzamide as a white solid.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationconcentrated
  3. customThe residue was purified by flash chromatography
  4. washeluting with 0-5% 2M NH3 in MeOH/CH2Cl2
  5. customThe product fractions were collected
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-2f9aadfc93c04703b348f6fa40bdc051
Source dataset
uspto-grants-2008_07
Patent number
US07405225B2

Reaction notes

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