1,1'-Carbonyldiimidazole → 2(3H)-Benzoxazolone, 5,7-dimethyl-

HRID 1442865Notes

Reaction equation

HRID 1442865 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([CH3:9])[C:3]=1[OH:10].[C:11](N1C=CN=C1)(N1C=CN=C1)=[O:12]>>[CH3:8][C:6]1[CH:5]=[C:4]([CH3:9])[C:3]2[O:10][C:11](=[O:12])[NH:1][C:2]=2[CH:7]=1

Participants

3

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 1005306-Amino-2,4-xylenol

Product 1

HCID 131175882(3H)-Benzoxazolone, 5,7-dimethyl-

Procedure

A mixture of 2-amino-4,6-dimethylphenol (412 mg, 3.00 mmol) and 1,1′-carbonyldiimidazole (730 mg, 4.50 mmol) in TIE (15 mL) was heated at reflux for 3 h. The mixture was allowed to cool, and the solvent removed under reduced pressure. The residue was taken up in EtOAc and washed with 1.0 N aqueous HCl (2×), then brine, then the EtOAc was dried over Na2SO4, filtered, and concentrated in vacuo to give the title compound. MS: m/z=164 (M+1).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 3 h
  3. temperatureto cool
  4. customthe solvent removed under reduced pressure
  5. washwashed with 1.0 N aqueous HCl (2×)
  6. dry with materialbrine, then the EtOAc was dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-de09c0aebd3b4a37bc5c9d4ae57a368a
Source dataset
uspto-grants-2010_02
Patent number
US07659300B2

Reaction notes

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