HQDA → HCID 131717194, compound

HRID 2372005Notes

Reaction equation

HRID 2372005 reaction equation
[CH:1]1[C:6]([O:7][C:8]2[CH:13]=[CH:12][C:11]3[C:14]([O:16][C:17](=[O:18])[C:10]=3[CH:9]=2)=[O:15])=[CH:5][CH:4]=[C:3]([O:19][C:20]2[CH:25]=[CH:24][C:23]3[C:26]([O:28][C:29](=[O:30])[C:22]=3[CH:21]=2)=[O:27])[CH:2]=1>CO>[CH:2]1[C:3]([O:19][C:20]2[CH:25]=[CH:24][C:23]3[C:26]([O:28][C:29](=[O:30])[C:22]=3[CH:21]=2)=[O:27])=[CH:4][CH:5]=[C:6]([O:7][C:8]2[CH:13]=[CH:12][C:11]3[C:14]([O:16][C:17](=[O:18])[C:10]=3[CH:9]=2)=[O:15])[CH:1]=1.[CH3:5][CH:6]([OH:7])[CH3:1].[CH:2]1[C:3]([O:19][C:20]2[CH:25]=[CH:24][C:23]3[C:26]([O:28][C:29](=[O:30])[C:22]=3[CH:21]=2)=[O:27])=[CH:4][CH:5]=[C:6]([O:7][C:8]2[CH:13]=[CH:12][C:11]3[C:14]([O:16][C:17](=[O:18])[C:10]=3[CH:9]=2)=[O:15])[CH:1]=1

Participants

3

Reactant 1

HCID 14549436HQDA3×

Product 1

HCID 131717194HCID 131717194, compoundYield 76.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

The product was a light tan solid containing a large amount (~232.8 g) of excess, unreacted HQDA. Since HQDA solubility in methanol (CH3OH) is ~6.3 weight percent at 23° C., >4.7 liters of CH3OH should dissolve all unreacted HQDA. Therefore, the product was crushed into a fine powder and washed with 2.8 liters of methanol by slurrying the powder in the methanol for several hours and suction filtering through a 25-50μ frit. It was then treated similarly four more times, using 1.2 liters of methanol per trituration. Hence, the product was washed with a total of 7.6 liters of methanol, or 2.9 liters more than the amount required to dissolve 233 g. The solid product was dried and yielded 192 g (76.8 percent of theoretical) of HQDA/IPA/HQDA. The light tan solid melted at 140°-155° C. on a Fisher Johns hot stage melting point apparatus. The melting point determined by DSC was 156°-161° C. Proton NMR was run in DMSO. The spectrum is in good agreement with the expected bis-paraacetoxy ended aromatic ester.

Workup

  1. customat 23° C.
  2. customTherefore, the product was crushed into a fine powder
  3. washwashed with 2.8 liters of methanol
  4. customfor several hours
  5. filtrationsuction filtering through a 25-50μ frit
  6. additionIt was then treated similarly four more times
  7. washHence, the product was washed with a total of 7.6 liters of methanol, or 2.9 liters more than the amount
  8. dissolutionto dissolve 233 g
  9. customThe solid product was dried

Sources & evidence

ORD record
ord-7e4167b7697a444bb1512745a7b265bf
Source dataset
uspto-grants-1992_03
Patent number
US05097010

Reaction notes

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