Acetic Acid → HCID 58737289, compound

HRID 722947Notes

Reaction equation

HRID 722947 reaction equation
[CH3:1][N:2]1[C:6]2[CH:7]=[C:8]3[C:13](=[CH:14][C:5]=2[N:4]([CH3:16])[C:3]1=[O:17])[C:12](=[O:15])[CH2:11][CH2:10][CH2:9]3.[C:18]([OH:21])(=[O:20])C.[H-].[Na+].O.O1CC[CH2:27][CH2:26]1>>[CH3:1][N:2]1[C:6]2[CH:7]=[C:8]3[C:13](=[CH:14][C:5]=2[N:4]([CH3:16])[C:3]1=[O:17])[C:12](=[O:15])[CH:11]([C:18]([O:21][CH2:26][CH3:27])=[O:20])[CH2:10][CH2:9]3

Participants

6

Reactant 5

HCID 176Acetic AcidHCID 962WaterHCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 21887257HCID 21887257, compound

Product 1

HCID 58737289HCID 58737289, compound

Procedure

60% Oily sodium hydride (6 g) was washed with n-hexane (2×30 ml), and the solvent was removed by decantation. Tetrahydrofuran (200 ml) and subsequently diethyl carbonate (9.8 g) were added thereto, and the mixture was refluxed gently. To the suspension was added dropwise a solution of 1,3-dimethyl-3,6,7,8-tetrahydro-1H-naphtho[2,3-d]imidazole-2,5-dione (10 g, 43.4 mmol) obtained in Reference Example 137 in hot tetrahydrofuran while maintaining refluxing. The mixture was refluxed for 18 hours, and allowed to cool, and then acetic acid (18 ml) was carefully added dropwise to decompose excessive sodium hydride. Further, water was added, extracted with ethyl acetate, and washed with brine. The organic layer was dried over anhydrous magnesium sulfate, the solvent was evaporated under reduced pressure, and the residue was crystallized from ethanol-diethyl ether to give the title compound as colorless crystals (7.0 g).

Workup

  1. wash60% Oily sodium hydride (6 g) was washed with n-hexane (2×30 ml)
  2. customthe solvent was removed by decantation
  3. additionTetrahydrofuran (200 ml) and subsequently diethyl carbonate (9.8 g) were added
  4. temperaturethe mixture was refluxed gently
  5. temperaturewhile maintaining
  6. temperaturerefluxing
  7. temperatureThe mixture was refluxed for 18 hours
  8. temperatureto cool
  9. extractionextracted with ethyl acetate
  10. washwashed with brine
  11. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  12. customthe solvent was evaporated under reduced pressure
  13. customthe residue was crystallized from ethanol-diethyl ether

Sources & evidence

ORD record
ord-fe2cd20a25fa4d818bb0b7783cdc68d9
Source dataset
uspto-grants-2006_11
Patent number
US07138533B2

Reaction notes

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