Hydrochloric Acid → HCID 10196854, compound

HRID 2307617Notes

Reaction equation

HRID 2307617 reaction equation
[CH:1]1[C:6]2[C:7]([O:9][C:10](=[O:11])[C:5]=2[CH:4]=[C:3]2[C:12]([O:14][C:15](=[O:16])[C:2]=12)=[O:13])=[O:8].C(N(CC)CC)C.[Cl:24][C:25]1[CH:49]=[CH:48][C:28]([O:29][C:30]2[CH:31]=[C:32]([CH:45]=[CH:46][CH:47]=2)[CH2:33][NH:34][C@@H:35]2[C:44]3[C:39](=[CH:40][CH:41]=[CH:42][CH:43]=3)[CH2:38][CH2:37][CH2:36]2)=[CH:27][CH:26]=1.C([O-])([O-])=[O:51].[Na+].[Na+].Cl>C1COCC1>[Cl:24][C:25]1[CH:26]=[CH:27][C:28]([O:29][C:30]2[CH:31]=[C:32]([CH:45]=[CH:46][CH:47]=2)[CH2:33][N:34]([C@@H:35]2[C:44]3[C:39](=[CH:40][CH:41]=[CH:42][CH:43]=3)[CH2:38][CH2:37][CH2:36]2)[C:7]([C:6]2[CH:1]=[C:2]([C:15]([OH:14])=[O:16])[C:3]([C:12]([OH:51])=[O:13])=[CH:4][C:5]=2[C:10]([OH:9])=[O:11])=[O:8])=[CH:48][CH:49]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 6966Pyromellitic dianhydrideHCID 8471TriethylamineHCID 10340Sodium CarbonateHCID 69722721HCID 69722721, compound

Product 1

HCID 10196854HCID 10196854, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

1,2,4,5-Benzenetetracarboxylic dianhydride (2.70 g, 12.4 mmol) and triethylamine (2.15 mL, 15.5 mmol) in THF (60 mL)were treated dropwise with the product from Example 1A (2.25 g, 6.18 mmol) in THF (10 mL) at −78° C. The reaction mixture was allowed to stir for 16 hours gradually warming to ambient temperature. The mixture was treated with saturated aqueous Na2CO3 solution, stirred vigorously for 30 minutes and then carefully acidified using 12M HCl. The acidified solution was extracted with ethyl acetate. The organic extracts were combined, washed with 1N HCl, brine, dried (Na2SO4), filtered and concentrated under reduced pressure. The residue was purified by flash chromatography (silica gel, 100:1:1 ethyl acetate:HCO2H:H2O) to provide the title compound as a white solid (1.92 g, 52% yield).

Workup

  1. stirringstirred vigorously for 30 minutes
  2. extractionThe acidified solution was extracted with ethyl acetate
  3. washwashed with 1N HCl, brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by flash chromatography (silica gel, 100:1:1 ethyl acetate:HCO2H:H2O)

Sources & evidence

ORD record
ord-b0aad1e6a31b4792b01c5f54948f3696
Source dataset
uspto-grants-2004_12
Patent number
US06831193B2

Reaction notes

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