Ethanol → N-(5,5-dimethyl-3-phenyl-[1,2,4]oxadiazol-4-yl)-3-ethyl-benzamide

HRID 339457Notes

Reaction equation

HRID 339457 reaction equation
[CH3:1][C:2]1([CH3:14])[O:6][N:5]=[C:4]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[N:3]1[NH2:13].C([C:17]1[CH:25]=[CH:24][C:20]([C:21](Cl)=[O:22])=[CH:19][CH:18]=1)C.[OH-].[Na+].[CH2:28](O)[CH3:29]>O>[CH3:1][C:2]1([CH3:14])[O:6][N:5]=[C:4]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[N:3]1[NH:13][C:21](=[O:22])[C:20]1[CH:19]=[CH:18][CH:17]=[C:25]([CH2:28][CH3:29])[CH:24]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 14798Sodium HydroxideHCID 853684-Ethylbenzoyl chlorideHCID 590166375,5-Dimethyl-3-phenyl-[1,2,4]oxadiazol-4-ylamine

Product 1

HCID 68955978N-(5,5-dimethyl-3-phenyl-[1,2,4]oxadiazol-4-yl)-3-ethyl-benzamide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To an ice-cold stirred solution of the 5,5-dimethyl-3-phenyl-[1,2,4]oxadiazol-4-ylamine (0.5 g, 2.6 mmol) in 6 mL of ethanol, was added an excess of 4-ethylbenzoyl chloride (4 mL), followed by aqueous NaOH (8%, 7 mL). The solution was stirred overnight and allowed to warm to room temperature. The mixture was diluted with water and extracted with CH2Cl2. The combined CH2Cl2 extracts were dried over MgSO4, and the solvent was removed in vacuo. The product, N-(5,5-dimethyl-3-phenyl-[1,2,4]oxadiazol-4-yl)-3-ethyl-benzamide, was isolated by silica gel chromatography. 1H-NMR (300 MHz, CDCl3) δ (ppm): 7.8 (m, 3H), 7.6 (d, 2H), 7.4 (m, 2H), 7.2 (d, 2H), 2.7 (q, 2H), 1.65 (s, 6H), 1.2 (t, 3H).

Workup

  1. extractionextracted with CH2Cl2
  2. dry with materialThe combined CH2Cl2 extracts were dried over MgSO4
  3. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-ad1967f3beee4a69ab36680fb9ceec23
Source dataset
uspto-grants-2014_11
Patent number
US08895306B2

Reaction notes

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