Acetic Acid → HCID 178515233, compound

HRID 357479Notes

Reaction equation

HRID 357479 reaction equation
[C:1]1([N:7]2[C:11](=[O:12])[C:10](=[CH:13][N:14]([CH3:16])C)[NH:9][C:8]2=[O:17])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[K].[O-][CH2:20][CH2:21][CH2:22][CH3:23].[C:24](O)(=O)C>CN(C)C=O.O1CCCC1>[C:1]1([N:7]2[C:11](=[O:12])[C:10]3=[CH:13][NH:14][C:16]4[CH2:23][CH2:22][CH2:21][CH2:20][C:24]=4[N:9]3[C:8]2=[O:17])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 5462222PotassiumHCID 12476378Butan-1-olateHCID 53692021HCID 53692021, compound

Product 1

HCID 178515233HCID 178515233, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-Phenyl-5-(dimethylaminomethylene)-imidazoline-2,4-dione (1.3 g) in dimethylformamide (20 mL) at 0° C was added 1M potassium terr-butoxide (5 mL ) in tetrahydrofuran. After 5 min 2-Chlorocycloxeanone (700 mg) was added and the mixture was stirred for 30 min. Acetic acid (1 mL) was added and the solvent was removed at reduced pressure. To the resulting residue was added ammonium acetate (10 gm) and acetic acid (25 ml) and the mixture was heated to reflux for 4 h. The solvent was removed at reduced pressure and water (50 mL) was added. The resulting solid was collected, washed with methanol and dried to yield 2-Phenyl-6,7,8,9-tetrahydro-imidazo[1,5,a]quinoxaline-1,3(2H,5H)-dione (Compound 21) as an off white solid. m.p. 236°-240° C.

Workup

  1. additionAfter 5 min 2-Chlorocycloxeanone (700 mg) was added
  2. customthe solvent was removed at reduced pressure
  3. additionTo the resulting residue was added ammonium acetate (10 gm) and acetic acid (25 ml)
  4. temperaturethe mixture was heated
  5. temperatureto reflux for 4 h
  6. customThe solvent was removed at reduced pressure and water (50 mL)
  7. additionwas added
  8. customThe resulting solid was collected
  9. washwashed with methanol
  10. customdried

Sources & evidence

ORD record
ord-127e21d8965948a3a69ebf84aec4887a
Source dataset
uspto-grants-1998_11
Patent number
US05840888

Reaction notes

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