Potassium Carbonate → HCID 68959534, compound

HRID 339454Notes

Reaction equation

HRID 339454 reaction equation
[CH2:1]([C:3]1[CH:11]=[CH:10][C:6](C(Cl)=O)=[CH:5][CH:4]=1)[CH3:2].[Cl:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2[N:23]([NH2:24])[C:22]([CH3:26])([CH3:25])[O:21][N:20]=2)=[CH:15][CH:14]=1.[C:27]([O-:30])([O-])=O.[K+].[K+]>C(OCC)(=O)C>[Cl:12][C:13]1[CH:14]=[CH:15][C:16]([C:19]2[N:23]([NH:24][C:27](=[O:30])[C:5]3[CH:6]=[CH:10][CH:11]=[C:3]([CH2:1][CH3:2])[CH:4]=3)[C:22]([CH3:26])([CH3:25])[O:21][N:20]=2)=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 853684-Ethylbenzoyl chlorideHCID 14684698HCID 14684698, compound

Product 1

HCID 68959534HCID 68959534, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

4-Ethylbenzoyl chloride (78.4 mg, 0.466 mmol) and 3-(4-chloro-phenyl)-5,5-dimethyl-[1,2,4]oxadiazol-4-ylamine (100 mg, 0.444 mmol) were dissolved in 4 mL of ethyl acetate in a 20 mL vial. With magnetic stirring, an aqueous solution of K2CO3 (2 mL, 0.166 g/mL) was added, and the mixture was stirred at room temperature for 18-64 hours. The reaction mixture was transferred to a separatory funnel. The organic phase was removed and evaporated to dryness under vacuum at room temperature and then at 50° C. for 30 minutes. The residue was triturated with a solution of 10% ether in hexane (7 mL) for 3-8 hours with magnetic stirring, and the resultant flocculent precipitate was removed and triturated again with 5% ether in hexane. Vacuum oven drying at 50° C. for 30 minutes yielded N-[3-(4-chloro-phenyl)-5,5-dimethyl-[1,2,4]oxadiazol-4-yl]-3-ethyl-benzamide in 90% purity. 1H-NMR (300 MHz, CDCl3) δ (ppm): 7.72 (d, 2H), 7.6 (d, 2H), 7.35 (d, 2H), 7.25 (d, 2H), 2.7 (q, 2H), 1.63 (s, 6H), 1.22 (t, 3H). Some analogs were purified by trituration with pentane, hexane, or heptane, or alternatively, by column chromatography using an ethyl acetate/hexane gradient.

Workup

  1. customThe reaction mixture was transferred to a separatory funnel
  2. customThe organic phase was removed
  3. customevaporated to dryness under vacuum at room temperature
  4. waitat 50° C. for 30 minutes
  5. customThe residue was triturated with a solution of 10% ether in hexane (7 mL) for 3-8 hours with magnetic stirring
  6. customthe resultant flocculent precipitate was removed
  7. customtriturated again with 5% ether in hexane
  8. customVacuum oven drying at 50° C. for 30 minutes

Sources & evidence

ORD record
ord-709c4c441ca141d3928e144502feed2c
Source dataset
uspto-grants-2014_11
Patent number
US08895306B2

Reaction notes

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