Benzene → HCID 86756098, compound

HRID 1274814Notes

Reaction equation

HRID 1274814 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([C:16]([F:19])([F:18])[F:17])[CH:11]=2)[N:6]=[C:5]([C:20]([NH:22][NH2:23])=[O:21])[CH:4]=1.[C:24]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)(=O)[CH3:25].O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C1C=CC=CC=1>C(OCC)(=O)C.O>[C:27]1([C:24](=[N:23][NH:22][C:20](=[O:21])[C:5]2[CH:4]=[C:3]([O:2][CH3:1])[CH:8]=[C:7]([O:9][C:10]3[CH:15]=[CH:14][CH:13]=[C:12]([C:16]([F:17])([F:18])[F:19])[CH:11]=3)[N:6]=2)[CH3:25])[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

6

Reactant 4

HCID 241BenzeneHCID 7410AcetophenoneHCID 521998p-Toluenesulfonic acid monohydrateHCID 70268884HCID 70268884, compound

Product 1

HCID 86756098HCID 86756098, compound

Reagents, catalysts & solvents 1

HCID 22728543Water ethylacetateSolvent

Procedure

4-methoxy-6-[3-(trifluoromethyl)phenoxy] picolinic acid hydrazide (0.30 g, 0.00092 mol) was mixed with acetophenone (0.11 ml, 0.00092×1.0 mol) and p-toluene sulfonic acid monohydrate (0.06 g, 0.00092×0.34 mol), and further with. benzene (about 20 ml). The obtained mixture was refluxed for about 3 hours so as to pass through a molecular sieve 4A. The obtained reaction solution was distributed in ethyl acetate-water, and the organic phase separated from the solution was washed with saturated brine, dried with anhydrous sodium sulfate and then concentrated. The obtained concentrated solution was purified by silica gel column chromatography (eluting solution: ethyl acetate/hexane), thereby obtaining an aimed product.

Workup

  1. temperatureThe obtained mixture was refluxed for about 3 hours so as
  2. customThe obtained reaction solution
  3. customthe organic phase separated from the solution
  4. washwas washed with saturated brine
  5. dry with materialdried with anhydrous sodium sulfate
  6. concentrationconcentrated
  7. customThe obtained concentrated solution was purified by silica gel column chromatography (eluting solution: ethyl acetate/hexane)

Sources & evidence

ORD record
ord-429886574d7149a09a7e8f26890680a8
Source dataset
uspto-grants-2000_12
Patent number
US06159901

Reaction notes

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