Chloroform → HCID 57463408, compound

HRID 339459Notes

Reaction equation

HRID 339459 reaction equation
[C:1](=[N:4][NH:5][C:6](=[O:16])[C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([O:13][CH3:14])[C:8]=1[CH3:15])([CH3:3])[CH3:2].Cl[O:18][N:19]=[CH:20][C:21]1[CH:26]=[C:25]([CH3:27])[CH:24]=[C:23]([CH3:28])[CH:22]=1.C(Cl)(Cl)Cl.C([O-])([O-])=O.[K+].[K+]>O>[CH3:28][C:23]1[CH:22]=[C:21]([C:20]2[N:4]([NH:5][C:6](=[O:16])[C:7]3[CH:12]=[CH:11][CH:10]=[C:9]([O:13][CH3:14])[C:8]=3[CH3:15])[C:1]([CH3:3])([CH3:2])[O:18][N:19]=2)[CH:26]=[C:25]([CH3:27])[CH:24]=1

Participants

6

Reactant 4

HCID 6212Chloroform2×HCID 11430Potassium CarbonateHCID 59016632HCID 59016632, compoundHCID 86594180HCID 86594180, compound

Product 1

HCID 57463408HCID 57463408, compoundYield 37.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

3-Methoxy-2-methyl-benzoic acid isopropylidene-hydrazide (1.71 g, 7.77 mmol) and 3,5-dimethyl-benzaldehyde chlorooxime (2.29 g, 12.4 mmol), both as CHCl3 solutions (total volume 40 mL), were added to a 250 mL round bottom flask equipped with a magnetic stirrer. An aqueous K2CO3 solution (5 g in 30 mL) was added, the vessel was placed in a 50° C. water bath, and the reaction was stirred vigorously for 24 hours. The reaction was monitored by 1H NMR. Chloroform (100 μl) and water (50 mL) were added, and the mixture was shaken in a separatory funnel. The organic phase was separated, dried, and the solvent was removed in vacuo. Column chromatography on silica gel using a gradient of 10-30% ethyl acetate in hexane yielded 1.07 g of N-[3-(3,5-dimethyl-phenyl)-5,5-dimethyl-[1,2,4]oxadiazol-4-yl]-3-methoxy-2-methyl-benzamide (32%). An analytical sample was obtained by crystallization from CH2Cl2/hexane under refrigeration. 1H NMR (300 MHz, CDCl3) δ (ppm): 7.4 (s, 2H), 7.1 (t, 1H), 7.07 (s, 1H), 6.85 (d, 1H), 6.65 (d, 1H), 3.78 (s, 3H), 2.30 (s, 6H), 2.07 (s, 3H), 1.65 (s, 6H).

Workup

  1. customequipped with a magnetic stirrer
  2. customwas placed in a 50° C.
  3. stirringthe mixture was shaken in a separatory funnel
  4. customThe organic phase was separated
  5. customdried
  6. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-581bade3aad14f27afadd0616f10a811
Source dataset
uspto-grants-2014_11
Patent number
US08895306B2

Reaction notes

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