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

HRID 1184308Notes

Reaction equation

HRID 1184308 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-9bb951f4e63146388c3fa9c33e3de85a
Source dataset
uspto-grants-2014_03
Patent number
US08669072B2

Reaction notes

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