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

HRID 968928Notes

Reaction equation

HRID 968928 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-463f9e18b58b455487519acc6da7c5bc
Source dataset
uspto-grants-2007_12
Patent number
US07304162B2

Reaction notes

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