4-Nitrophenol → 4-Nitrophenyl 6-chloro-2-(4,6-dimethoxypyrimidin-2-yloxy)benzoate

HRID 1885961Notes

Reaction equation

HRID 1885961 reaction equation
[Cl:1][C:2]1[C:7]([C:8]([OH:10])=[O:9])=[C:6]([O:11][C:12]2[N:17]=[C:16]([O:18][CH3:19])[CH:15]=[C:14]([O:20][CH3:21])[N:13]=2)[CH:5]=[CH:4][CH:3]=1.[N+:22]([C:25]1[CH:30]=[CH:29][C:28](O)=[CH:27][CH:26]=1)([O-:24])=[O:23].C1(N=C=NC2CCCCC2)CCCCC1>C(Cl)Cl>[Cl:1][C:2]1[C:7]([C:8]([O:10][C:28]2[CH:29]=[CH:30][C:25]([N+:22]([O-:24])=[O:23])=[CH:26][CH:27]=2)=[O:9])=[C:6]([O:11][C:12]2[N:13]=[C:14]([O:20][CH3:21])[CH:15]=[C:16]([O:18][CH3:19])[N:17]=2)[CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 9804-NitrophenolHCID 10868DicyclohexylcarbodiimideHCID 156119442-Chloro-6-((4,6-dimethoxypyrimidin-2-yl)oxy)benzoic acid

Product 1

HCID 198765994-Nitrophenyl 6-chloro-2-(4,6-dimethoxypyrimidin-2-yloxy)benzoateYield 73.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of 5.4 grams (0.017 mole) of 6-chloro-2-(4,6-dimethoxypyrimidin-2-yloxy)benzoic acid in 25 mL of methylene chloride was added 2.4 grams (0.017 mole) of 4-nitrophenol. The reaction mixture was cooled to 0° C., and 3.5 grams (0.017 mole) of dicyclohexylcarbodiimide was added. Upon completion of addition, the reaction mixture was stirred at 0° C. for 30 minutes, and then it was warmed to ambient temperature where it was stirred for an additional two hours. The reaction mixture was filtered, and the filtrate was concentrated under reduced pressure to a residue. The residue was stirred with diethyl ether, and the resultant solid was collected by filtration to yield 5.4 grams of 4-nitrophenyl 6-chloro-2-(4,6-dimethoxypyrimidin-2-yloxy)benzoate, m.p. 130°-132° C. The nmr spectrum was consistent with the proposed structure.

Workup

  1. additionUpon completion of addition
  2. temperatureit was warmed to ambient temperature where it
  3. stirringwas stirred for an additional two hours
  4. filtrationThe reaction mixture was filtered
  5. concentrationthe filtrate was concentrated under reduced pressure to a residue
  6. stirringThe residue was stirred with diethyl ether
  7. filtrationthe resultant solid was collected by filtration

Sources & evidence

ORD record
ord-63ec0cdfc92d45529dc2095dab6251a7
Source dataset
uspto-grants-1992_09
Patent number
US05149357

Reaction notes

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