Benzene → HCID 86756097, compound

HRID 1274812Notes

Reaction equation

HRID 1274812 reaction equation
CO[CH:3](OC)[CH2:4][C:5]#[N:6].C1C=CC=CC=1.[CH3:15][O:16][C:17]1[CH:22]=[C:21]([O:23][C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([C:30]([F:33])([F:32])[F:31])[CH:25]=2)[N:20]=[C:19]([C:34]([NH:36][NH2:37])=[O:35])[CH:18]=1>Cl.C(OCC)(=O)C.O>[C:5]([CH2:4][CH:3]=[N:37][NH:36][C:34](=[O:35])[C:19]1[CH:18]=[C:17]([O:16][CH3:15])[CH:22]=[C:21]([O:23][C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([C:30]([F:31])([F:32])[F:33])[CH:25]=2)[N:20]=1)#[N:6]

Participants

6

Reactant 3

HCID 241BenzeneHCID 937313,3-DimethoxypropiononitrileHCID 70268884HCID 70268884, compound

Product 1

HCID 86756097HCID 86756097, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 22728543Water ethylacetateSolvent

Conditions

Temperature
55 °C

Procedure

3,3-dimethoxy propionitrile (0.35 g, 0.0015×2 mol) was dissolved in a 2N aqueous hydrochloric acid solution (about 10 ml). The obtained solution was stirred at a temperature of about 50 to 60° C. for about one hour. The solution was further mixed with benzene (about 10 ml) and 4-methoxy-6-[3-(trifluoromethyl)phenoxy] picolinic acid hydrazide (0.50 g, 0.0015 mol), and then the resultant mixture was stirred at that temperature for about one hour. The obtained reaction solution was distributed in ethyl acetate-water The organic phase separated from the solution was successively washed with saturated sodium bicarbonate water and with saturated brine, and then dried with anhydrous sodium sulfate. Thereafter, the resultant solution was concentrated and then purified by silica gel column chromatography (eluting solution: ethyl acetate/hexane), thereby obtaining an aimed product.

Workup

  1. customThe obtained reaction solution
  2. customseparated from the solution
  3. washwas successively washed with saturated sodium bicarbonate water and with saturated brine
  4. dry with materialdried with anhydrous sodium sulfate
  5. concentrationThereafter, the resultant solution was concentrated
  6. custompurified by silica gel column chromatography (eluting solution: ethyl acetate/hexane)

Sources & evidence

ORD record
ord-39ae241fe19a48af9ac2212ae0e7915e
Source dataset
uspto-grants-2000_12
Patent number
US06159901

Reaction notes

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