Water → HCID 59016634, compound

HRID 1184306Notes

Reaction equation

HRID 1184306 reaction equation
[OH-].[Na+].[CH3:3][C:4]1[CH:5]=[C:6]([C:11]2[N:15]([NH2:16])[C:14]([CH3:18])([CH3:17])[O:13][N:12]=2)[CH:7]=[C:8]([CH3:10])[CH:9]=1.[CH2:19]([C:21]1[C:29]([O:30][CH3:31])=[CH:28][CH:27]=[CH:26][C:22]=1[C:23](Cl)=[O:24])[CH3:20].O>C1(C)C=CC=CC=1.C(Cl)(Cl)Cl>[CH3:3][C:4]1[CH:5]=[C:6]([C:11]2[N:15]([NH:16][C:23](=[O:24])[C:22]3[CH:26]=[CH:27][CH:28]=[C:29]([O:30][CH3:31])[C:21]=3[CH2:19][CH3:20])[C:14]([CH3:18])([CH3:17])[O:13][N:12]=2)[CH:7]=[C:8]([CH3:10])[CH:9]=1

Participants

7

Reactant 4

HCID 962WaterHCID 14798Sodium Hydroxide2×HCID 221445622-Ethyl-3-methoxybenzoyl chlorideHCID 59016633HCID 59016633, compound

Product 1

HCID 59016634HCID 59016634, compoundYield 29%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6212ChloroformSolvent

Procedure

A 20% aqueous solution of NaOH (275 mg, 1.37 mmol) was added to a solution of 3-(3,5-dimethyl-phenyl)-5,5-dimethyl-[1,2,4]oxadiazol-4-ylamine (200 mg, 0.91 mmol) in 2 mL of toluene. 2-Ethyl-3-methoxybenzoyl chloride (199 mg, 1 mmol) was then added to the mixture. The reaction was stirred at room temperature for 2 hours, and then heated at 50° C. for 1 hour. TLC indicated 3 spots. Water, dilute NaOH, and CHCl3 were then added to the reaction mixture. The organic phase was separated, dried over MgSO4, and the solvent removed in vacuo. The residue was triturated with 10% ether in hexane. Filtration and air-drying of the resultant solid provided 100 mg (29% yield) of N-[3-(3,5-dimethyl-phenyl)-5,5-dimethyl-[1,2,4]oxadiazol-4-yl]-2-ethyl-3-methoxy-benzamide. 1H-NMR (300 MHz, CDCl3) δ (ppm): 7.42 (s, 2H), 7.11 (s, 1H), 7.11 (t, 1H), 6.9 (d, 1H), 6.67 (d, 1H), 3.81 (s, 3H), 2.55 (q, 2H), 2.34 (s, 6H), 1.7 (br s, 6H), 1.05 (t, 3H), Rf=0.5 (1:1 ethyl acetate:hexane).

Workup

  1. temperatureheated at 50° C. for 1 hour
  2. customThe organic phase was separated
  3. dry with materialdried over MgSO4
  4. customthe solvent removed in vacuo
  5. customThe residue was triturated with 10% ether in hexane
  6. filtrationFiltration
  7. customair-drying of the resultant solid

Sources & evidence

ORD record
ord-d941fcc4a6e144cf87b42cfa414076ab
Source dataset
uspto-grants-2014_03
Patent number
US08669072B2

Reaction notes

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