Water → HCID 59016634, compound

HRID 1184307Notes

Reaction equation

HRID 1184307 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 HydroxideHCID 221445622-Ethyl-3-methoxybenzoyl chlorideHCID 59016633HCID 59016633, compound

Product 1

HCID 59016634HCID 59016634, compoundYield 40%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6212ChloroformSolvent

Procedure

A 5% aqueous solution of NaOH (4 mL) was added to a solution of 3-(3,5-dimethyl-phenyl)-5,5-dimethyl-[1,2,4]oxadiazol-4-ylamine (90 mg) in 6 mL of toluene. 2-Ethyl-3-methoxybenzoyl chloride (140 mg) was then added to the mixture. The reaction was stirred at room temperature for 30 hours. Water and CHCl3 were added. The organic phase was separated, dried over MgSO4, and the solvent was removed in vacuo. The residue was triturated with 100 mL of 10% ether in hexane by magnetic stirring of the mixture in a vessel for 1 hour. Filtration and air-drying of the resultant solid provided 62 mg (40% 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). The filtrate contained an additional quantity of the intended product.

Workup

  1. customThe organic phase was separated
  2. dry with materialdried over MgSO4
  3. customthe solvent was removed in vacuo
  4. customThe residue was triturated with 100 mL of 10% ether in hexane
  5. stirringby magnetic stirring of the mixture in a vessel for 1 hour
  6. filtrationFiltration
  7. customair-drying of the resultant solid

Sources & evidence

ORD record
ord-5c2ddd6177544844966e8ec707e4921f
Source dataset
uspto-grants-2014_03
Patent number
US08669072B2

Reaction notes

Loading…