1,1'-Carbonyldiimidazole → 4,5-Dihydro-7H-imidazo[4,5,1-jk][4,1]benzoxazepine-2,7(1H)-dione

HRID 1698540Notes

Reaction equation

HRID 1698540 reaction equation
[NH2:1][C:2]1[C:12]2[NH:11][CH2:10][CH2:9][O:8][C:7](=[O:13])[C:6]=2[CH:5]=[CH:4][CH:3]=1.[C:14](N1C=CN=C1)(N1C=CN=C1)=[O:15]>C1COCC1>[NH:1]1[C:2]2=[CH:3][CH:4]=[CH:5][C:6]3=[C:12]2[N:11]([CH2:10][CH2:9][O:8][C:7]3=[O:13])[C:14]1=[O:15]

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 672729029-Amino-2,3-dihydro-4,1-benzoxazepin-5(1H)-one

Product 1

HCID 672729594,5-Dihydro-7H-imidazo[4,5,1-jk][4,1]benzoxazepine-2,7(1H)-dioneYield 123.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 200 mg (1.13 mmol) of 9-amino-2,3-dihydro-4,1-benzoxazepin-5(1H)-one in 20 mL of THF was added 280 mg (2 mmol) of 1,1′-carbonyldiimidazole and the reaction mixture was stirred overnight at room temperature. The reaction mixture was heated at 50° C. for 4 h and allowed to cool to room temperature. The reaction was concentrated in vacuo and the residue was dissolved in a mixture of ethyl acetate/n-hexane (1:1) and washed with water. The organics were dried over sodium sulfate, filtered, and concentrated in vacuo to give 286 mg (1.40 mmol, 70%) of the title compound.

Workup

  1. temperatureThe reaction mixture was heated at 50° C. for 4 h
  2. temperatureto cool to room temperature
  3. concentrationThe reaction was concentrated in vacuo
  4. dissolutionthe residue was dissolved in a mixture of ethyl acetate/n-hexane (1:1)
  5. washwashed with water
  6. dry with materialThe organics were dried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e4f9eca2ff744d91aed79647108833ce
Source dataset
uspto-grants-2012_04
Patent number
US08163935B2

Reaction notes

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