1,1'-Carbonyldiimidazole → HCID 15588673, compound

HRID 636509Notes

Reaction equation

HRID 636509 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([O:8][CH:9]2[CH2:14][CH2:13][CH2:12][CH2:11][O:10]2)[C:3]=1[OH:15].[C:16](N1C=CN=C1)(N1C=CN=C1)=[O:17]>O1CCCC1>[O:10]1[CH2:11][CH2:12][CH2:13][CH2:14][CH:9]1[O:8][C:4]1[C:3]2[O:15][C:16](=[O:17])[NH:1][C:2]=2[CH:7]=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 21254739HCID 21254739, compound

Product 1

HCID 15588673HCID 15588673, compoundYield 87.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-amino-6-(tetrahydropyran-2-yloxy)phenol (2.0 g) in anhydrous tetrahydrofuran (30 ml) was added 1,1′-carbonyldiimidazole (2.03 g), and the mixture was refluxed for 2 hours under nitrogen atmosphere. After cooling, the reaction mixture was concentrated in vacuo. The residue was purified by flash chromatography (chloroform:methanol=40:1, v/v) and crystallized with diisopropyl ether to give 7-(tetrahydropyran-2-yloxy)-2(3H)-benzoxazolone (1.96 g).

Workup

  1. temperaturethe mixture was refluxed for 2 hours under nitrogen atmosphere
  2. temperatureAfter cooling
  3. concentrationthe reaction mixture was concentrated in vacuo
  4. customThe residue was purified by flash chromatography (chloroform
  5. custommethanol=40:1, v/v) and crystallized with diisopropyl ether

Sources & evidence

ORD record
ord-b1001d9e55a54579b3dcbaf4451cb596
Source dataset
uspto-grants-2001_02
Patent number
US06194396B1

Reaction notes

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