1,1'-Carbonyldiimidazole → 6-Methyl-5-(methyloxy)-1,3-benzoxazol-2(3H)-one

HRID 2354355Notes

Reaction equation

HRID 2354355 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[C:5]([CH3:10])=[CH:4][C:3]=1[OH:11].C1N=CN([C:17](N2C=NC=C2)=[O:18])C=1>C1COCC1>[CH3:10][C:5]1[C:6]([O:8][CH3:9])=[CH:7][C:2]2[NH:1][C:17](=[O:18])[O:11][C:3]=2[CH:4]=1

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 130767582-Amino-4-methoxy-5-methylphenol

Product 1

HCID 574186666-Methyl-5-(methyloxy)-1,3-benzoxazol-2(3H)-oneYield 98.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-amino-5-methyl-4-(methyloxy)phenol (1.54 g, 10 mmol) in THF (60 mL) was added carbodiimidazole (1.94 g, 12 mmol). The reaction mixture was stirred for 3 hours at room temperature, concentrated, diluted with EtOAc (100 mL), washed with 1N HCl, H2O, brine, and dried (Na2SO4). The solvent was removed via rotovap to give the title compound (1.76 g, 98%) as a white solid. MS (ES) m/e 180 [M+H]+.

Workup

  1. concentrationconcentrated
  2. additiondiluted with EtOAc (100 mL)
  3. washwashed with 1N HCl, H2O, brine
  4. dry with materialdried (Na2SO4)
  5. customThe solvent was removed via rotovap

Sources & evidence

ORD record
ord-812da07e70064f6b93c9dead3abc0f84
Source dataset
uspto-grants-2010_07
Patent number
US07749998B2

Reaction notes

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