Acetone → HCID 67000515, compound

HRID 561090Notes

Reaction equation

HRID 561090 reaction equation
[Br:1][C:2]1[CH:27]=[CH:26][C:5]([CH2:6][CH:7]2[CH2:12][CH2:11][N:10]([CH2:13][CH2:14][C:15]3[CH:16]=[C:17]4[C:22](=[CH:23][CH:24]=3)[O:21][CH2:20][CH2:19][C:18]4=[O:25])[CH2:9][CH2:8]2)=[CH:4][C:3]=1[O:28][CH2:29][CH2:30][O:31][CH3:32].[C:33]([OH:40])(=[O:39])/[CH:34]=[CH:35]/[C:36]([OH:38])=[O:37].CC(C)=O>C(O)C.CO>[C:33]([OH:40])(=[O:39])/[CH:34]=[CH:35]/[C:36]([OH:38])=[O:37].[Br:1][C:2]1[CH:27]=[CH:26][C:5]([CH2:6][CH:7]2[CH2:12][CH2:11][N:10]([CH2:13][CH2:14][C:15]3[CH:16]=[C:17]4[C:22](=[CH:23][CH:24]=3)[O:21][CH2:20][CH2:19][C:18]4=[O:25])[CH2:9][CH2:8]2)=[CH:4][C:3]=1[O:28][CH2:29][CH2:30][O:31][CH3:32]

Participants

6

Reactant 3

HCID 180AcetoneHCID 444972Fumaric AcidHCID 44182694HCID 44182694, compound

Product 1

HCID 67000515HCID 67000515, compoundYield 88%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 887MethanolSolvent

Procedure

The compound (3.0 g, 6.0 mmol) obtained in Example 3 was dissolved in ethanol (75 mL), and a solution of fumaric acid (693 mg, 6.0 mmol) in ethanol (25 mL) and further methanol (100 mL) were added thereto. The dissolution thereof was confirmed, and the solvent was then distilled off under reduced pressure to obtain a concentrated residue. To this concentrated residue, acetone (110 mL) was added, and the mixture was stirred at room temperature for 2.5 hours. The resulting precipitate was collected by filtration and dried under reduced pressure (40° C., 1 mmHg, 18 hours) to obtain the title compound (3.26 g, 88%) as a colorless crystalline solid.

Workup

  1. dissolutionThe dissolution
  2. distillationthe solvent was then distilled off under reduced pressure
  3. customto obtain a concentrated residue
  4. filtrationThe resulting precipitate was collected by filtration
  5. customdried under reduced pressure (40° C., 1 mmHg, 18 hours)

Sources & evidence

ORD record
ord-f0397b7b9f0942c3932b58d4f1ae3316
Source dataset
uspto-grants-2011_11
Patent number
US08063223B2

Reaction notes

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