Pyridine → HCID 20786539, compound

HRID 2182891Notes

Reaction equation

HRID 2182891 reaction equation
Cl[S:2]([C:5]1[C:16]([CH3:17])=[CH:15][C:8]([O:9][CH2:10][C:11]([O:13][CH3:14])=[O:12])=[CH:7][C:6]=1[CH3:18])(=[O:4])=[O:3].[CH3:19][O:20][C:21]1[CH:27]=[CH:26][C:24]([NH2:25])=[C:23]([N+:28]([O-:30])=[O:29])[CH:22]=1.N1C=CC=CC=1>C1(C)C=CC=CC=1>[CH3:19][O:20][C:21]1[CH:27]=[CH:26][C:24]([NH:25][S:2]([C:5]2[C:16]([CH3:17])=[CH:15][C:8]([O:9][CH2:10][C:11]([O:13][CH3:14])=[O:12])=[CH:7][C:6]=2[CH3:18])(=[O:4])=[O:3])=[C:23]([N+:28]([O-:30])=[O:29])[CH:22]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 667934-Methoxy-2-nitroanilineHCID 20786562Methyl [4-(chlorosulfonyl)-3,5-dimethylphenoxy]acetate2×

Product 1

HCID 20786539HCID 20786539, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of methyl (4-chlorosulfonyl-3,5-dimethylphenoxy)acetate (Intermediate A1, 7.6 g, 0.026 mol), 4-methoxy-2-nitroaniline (4.0 g, 0.024 mol), and pyridine (50 mL) was stirred at room temperature for 16 hr, in a 90° C. bath for 5 hr, and in a 130° C. bath for 30 min. The mixture was cooled and stirred with toluene for 10 min. The resulting suspension was filtered, and the filtrate was concentrated, diluted with 150 mL toluene and 100 mL ethyl acetate, washed with 1 M hydrochloric acid and water, and concentrated to about 50 mL. The mixture was left overnight in a freezer. The solid was collected and washed with several portions of cold toluene. After drying, it weighed 8.2 g (74%). Another 0.45 g portion of the title compound was recovered from extraction of aqueous phases and crystallization of a second crop from the toluene filtrate.

Workup

  1. waitin a 130° C. bath for 30 min
  2. temperatureThe mixture was cooled
  3. filtrationThe resulting suspension was filtered
  4. concentrationthe filtrate was concentrated
  5. additiondiluted with 150 mL toluene and 100 mL ethyl acetate
  6. washwashed with 1 M hydrochloric acid and water
  7. concentrationconcentrated to about 50 mL
  8. waitThe mixture was left overnight in a freezer
  9. customThe solid was collected
  10. washwashed with several portions of cold toluene
  11. customAfter drying
  12. customAnother 0.45 g portion of the title compound was recovered from extraction of aqueous phases and crystallization of a second crop from the toluene filtrate

Sources & evidence

ORD record
ord-43c026c1a2e54e3485b72943114f7568
Source dataset
uspto-grants-2005_05
Patent number
US06897227B2

Reaction notes

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