4-Nitrophenol → HCID 57814655, compound

HRID 521615Notes

Reaction equation

HRID 521615 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:32]=[CH:33][CH:34]=1)[C:6]([NH:8][C:9]1[CH:25]=[CH:24][C:12]([O:13][CH2:14][CH2:15][NH:16][C:17](=[O:23])[O:18][C:19](Cl)(Cl)Cl)=[C:11]([C:26]2[N:30]([CH3:31])[N:29]=[CH:28][CH:27]=2)[CH:10]=1)=[O:7].[N+:35]([C:38]1[CH:43]=[CH:42]C(O)=[CH:40][CH:39]=1)([O-:37])=[O:36].[O-2].[Mg+2]>C(OCC)(=O)C>[N+:35]([C:38]1[CH:43]=[CH:42][C:19]([O:18][C:17](=[O:23])[NH:16][CH2:15][CH2:14][O:13][C:12]2[CH:24]=[CH:25][C:9]([NH:8][C:6](=[O:7])[C:5]3[CH:32]=[CH:33][CH:34]=[C:3]([O:2][CH3:1])[CH:4]=3)=[CH:10][C:11]=2[C:26]2[N:30]([CH3:31])[N:29]=[CH:28][CH:27]=2)=[CH:40][CH:39]=1)([O-:37])=[O:36]

Participants

5

Reactant 3

HCID 9804-NitrophenolHCID 6850729Magnesium monoxideHCID 67265469HCID 67265469, compound

Product 1

HCID 57814655HCID 57814655, compoundYield 39.1%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
22 °C

Procedure

Trichloromethyl 2-(4-(3-methoxybenzamido)-2-(1-methyl-1H-pyrazol-5-yl)phenoxy)ethylcarbamate (50.0 g, 94.74 mmol), 4-nitrophenol (14.50 g, 1.1 eq) and magnesium oxide (1.067 mL, 1.0 eq) were taken up in 2 mL of ethyl acetate in a round bottomed flask and stirred at 22° C. for 3 hr. The magnesium oxide was filtered off. The solvent was then evaporated and it was purified by HPLC. The proper fractions were collected and lyophilized to afford the title compound as a white solid in 39.1% yield. LCMS m/z (%)=532 (M+H, 100).

Workup

  1. filtrationThe magnesium oxide was filtered off
  2. customThe solvent was then evaporated
  3. customit was purified by HPLC
  4. customThe proper fractions were collected

Sources & evidence

ORD record
ord-34f067070ed240aa98819bfc0fbd0c9a
Source dataset
uspto-grants-2016_05
Patent number
US09328107B2

Reaction notes

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