Potassium Carbonate → HCID 58913171, compound

HRID 1296551Notes

Reaction equation

HRID 1296551 reaction equation
[C:1](=[O:4])([O-])[O-].[K+].[K+].[CH2:7]([O:14][CH2:15][C@H:16]1[O:18][C@H:17]1[CH2:19][O:20][C:21](=[O:31])NC(=O)C1C=CC=CC=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[Cl-].[NH4+:33]>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.C(#N)C>[C:21]([O:20][CH2:19][C@@H:17]1[C@@H:16]([CH2:15][O:14][CH2:7][C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[O:18][C:1](=[O:4])[NH:33]1)(=[O:31])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 25517Ammonium ChlorideHCID 15923965HCID 15923965, compound

Product 1

HCID 58913171HCID 58913171, compound

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 6342AcetonitrileSolvent

Procedure

Potassium carbonate (4.04 g, 29.2 mmol) and tetrabutylammonium iodide (800 mg, 2.2 mmol) were added to an acetonitrile solution (100 mL) containing 5.8 g of benzoylcarbamate (2), and the mixture was stirred at room temperature for 18 hours. Saturated ammonium chloride aqueous solution was added to the reaction solution to quench the reaction. After ether extraction, the organic layer was dried over magnesium sulfate. The solvent was distilled off and the resulting residue was purified by silica gel column chromatography (ether/hexane=2/1) to obtain 4.87 g of a mixture of the title compounds (3 steps, 98%).

Workup

  1. customto quench
  2. customthe reaction
  3. extractionAfter ether extraction
  4. dry with materialthe organic layer was dried over magnesium sulfate
  5. distillationThe solvent was distilled off
  6. customthe resulting residue was purified by silica gel column chromatography (ether/hexane=2/1)

Sources & evidence

ORD record
ord-1dd842ece06449ba903da87758e06ffd
Source dataset
uspto-grants-2007_07
Patent number
US07247652B2

Reaction notes

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