Pyromellitic dianhydride → HCID 10128976, compound

HRID 2307720Notes

Reaction equation

HRID 2307720 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([O:7][C:8]2[CH:9]=[C:10]([CH:23]=[CH:24][CH:25]=2)[CH2:11][NH:12][C@@H:13]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[CH2:16][CH2:15][CH2:14]2)=[CH:3][CH:2]=1.C(N(C(C)C)CC)(C)C.[CH:35]1[C:40]2[C:41]([O:43][C:44](=[O:45])[C:39]=2[CH:38]=[C:37]2[C:46]([O:48][C:49](=[O:50])[C:36]=12)=[O:47])=[O:42].C([O-])([O-])=[O:52].[Na+].[Na+]>C1COCC1>[N:1]1[CH:2]=[CH:3][C:4]([O:7][C:8]2[CH:9]=[C:10]([CH:23]=[CH:24][CH:25]=2)[CH2:11][N:12]([C@@H:13]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[CH2:16][CH2:15][CH2:14]2)[C:41]([C:40]2[CH:35]=[C:36]([C:49]([OH:48])=[O:50])[C:37]([C:46]([OH:52])=[O:47])=[CH:38][C:39]=2[C:44]([OH:43])=[O:45])=[O:42])=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 6966Pyromellitic dianhydrideHCID 10340Sodium CarbonateHCID 81531DiisopropylethylamineHCID 69721082HCID 69721082, compound

Product 1

HCID 10128976HCID 10128976, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The product from Example 106A (1.17 g), diisopropylethyl amine (2.5 mL, 14.4 mmol) and 1,2,4,5-benzenetetracarboxylic dianhydride (0.78 g, 3.58 mmol) in THF (30 mL) were processed as described in Example 1B. The reaction mixture was treated with saturated Na2CO3 solution (30 mL), and stirred vigorously at room temperature for 1 hour. The layers were separated and the aqueous layer was acidified with 1N HCl. The acidified aqueous layer was evaporated under reduced pressure to afford off-white plates. Soxhlet extraction (ethanol) of the crude solid, followed by RP-HPLC, provided the title compound (20 mg).

Workup

  1. customThe layers were separated
  2. customThe acidified aqueous layer was evaporated under reduced pressure
  3. customto afford off-white plates
  4. extractionSoxhlet extraction (ethanol) of the crude solid

Sources & evidence

ORD record
ord-af4788b417bf493980a035f5af43e3ca
Source dataset
uspto-grants-2004_12
Patent number
US06831193B2

Reaction notes

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