Tetrahydrofuran → 3,3a-Dihydro-1H-oxazolo[3,4-a]quinoxaline-1,4(5H)-dione

HRID 1899955Notes

Reaction equation

HRID 1899955 reaction equation
[CH3:1][O:2][C:3](=O)[CH:4]([CH2:15][OH:16])[NH:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[N+:12]([O-])=O.C(N1C=CN=C1)(N1C=CN=C1)=[O:19].C1COCC1>C(N(CC)CC)C>[C:1]1(=[O:19])[N:5]2[C:6]3[C:7]([NH:12][C:15](=[O:16])[CH:4]2[CH2:3][O:2]1)=[CH:8][CH:9]=[CH:10][CH:11]=3

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 682631,1'-Carbonyldiimidazole2×HCID 10014501HCID 10014501, compound

Product 1

HCID 104428883,3a-Dihydro-1H-oxazolo[3,4-a]quinoxaline-1,4(5H)-dione

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

To 3-hydroxymethyl-1,2,3,4-tetrahydroquinoxalin-2-one (IV, EXAMPLE 286, 1.35 g), 1.00 g of carbonyldiimidazole, and 30 ml of THF are added 1.64 ml of triethylamine. The reaction is stirred at 20°-25° for 6 hr, then at 80° for 18 hr, at which time an additional 0.11 g carbonyldiimidazole are added. Heating is continued for another 6 hr, at which time the reaction mixture is cooled and the solvent is removed under reduced pressure. The residue is partitioned between methylene chloride and water, the organic layers are dried over sodium sulfate and concentrated. The residue is crystallized from methanol/dichloromethane to give the title compound, mp 230°-231°; MS (m/z) at 204; NMR (CDCl3) 4.60, 4.78, 6.93, 7.19, 7.82 and 8.48 δ.

Workup

  1. waitat 80° for 18 hr
  2. temperatureHeating
  3. waitis continued for another 6 hr, at which time
  4. temperaturethe reaction mixture is cooled
  5. customthe solvent is removed under reduced pressure
  6. customThe residue is partitioned between methylene chloride and water
  7. dry with materialthe organic layers are dried over sodium sulfate
  8. concentrationconcentrated
  9. customThe residue is crystallized from methanol/dichloromethane

Sources & evidence

ORD record
ord-8c0c705e0225498792a77c2a834aeeea
Source dataset
uspto-grants-1996_11
Patent number
US05574038

Reaction notes

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