4-Nitrophenol → HCID 131723616, compound

HRID 896992Notes

Reaction equation

HRID 896992 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[C:2]1[S:10]([N:13]([CH2:15][P:16](=[O:19])([OH:18])[OH:17])[CH3:14])(=[O:12])=[O:11].[CH:20]1[C:25]([N+:26]([O-:28])=[O:27])=[CH:24][CH:23]=[C:22](O)[CH:21]=1.ClC(Cl)(Cl)C#N>N1C=CC=CC=1>[NH4+:13].[N+:26]([C:25]1[CH:20]=[CH:21][C:22]([O:19][P:16]([CH2:15][N:13]([S:10]([C:2]2[S:1][C:5]3[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=3[CH:3]=2)(=[O:11])=[O:12])[CH3:14])(=[O:18])[O-:17])=[CH:23][CH:24]=1)([O-:28])=[O:27]

Participants

5

Reactant 3

HCID 9804-NitrophenolHCID 11011TrichloroacetonitrileHCID 22179272HCID 22179272, compound

Product 1

HCID 131723616HCID 131723616, compoundYield 173%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
107.5 °C

Procedure

A reaction mixture consisting of 500 mg (1.56 mmol) of (xv), 265 mg (1.90 mmol) of p-nitrophenol, 1.1 mL (11 mmol) of trichloroacetonitrile, and 5 mL of anhydrous pyridine was stirred in a sealed tube for 5 hours at 105-110° C. After the reaction was complete, pyridine was evaporated in vacuum, the oily residue was chromatographed on a silica gel column, eluent chloroform/MeOH/ammonium hydroxide (9:2:0.1) to yield 620 mg (87%) of the title compound as a pale crystalline substance: 1H NMR: (300 MHz, DMSO-d6) δH 2.89 (s, CH3), 3.07 (d, J=11.5 Hz, 2H), 7.15 (br s, 4H, NH4), 7.37 (d, J=9.3 Hz, 2H, Ar—H), 7.47-7.57 (m, 2H, Ar—H), 8.01-8.14 (m, 5 H, Ar—H).

Workup

  1. custompyridine was evaporated in vacuum
  2. customthe oily residue was chromatographed on a silica gel column, eluent chloroform/MeOH/ammonium hydroxide (9:2:0.1)

Sources & evidence

ORD record
ord-da72a563f79044b8846dd9e8c70017d8
Source dataset
uspto-grants-2005_07
Patent number
US06921756B2

Reaction notes

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