Water → Methyl 3-{5-[(2,4-dichloro-m-tolyl)oxy]-2-nitrophenyl}tetrahydro-5-methyl-2,4,6-trioxo-s-triazine-1(2H)-acetate

HRID 440552Notes

Reaction equation

HRID 440552 reaction equation
F[C:2]1[CH:3]=[CH:4][C:5]([N+:23]([O-:25])=[O:24])=[C:6]([N:8]2[C:13](=[O:14])[N:12]([CH3:15])[C:11](=[O:16])[N:10]([CH2:17][C:18]([O:20][CH3:21])=[O:19])[C:9]2=[O:22])[CH:7]=1.[Cl:26][C:27]1[C:32](C)=[C:31]([Cl:34])[CH:30]=[CH:29][C:28]=1O.[C:36](=O)([O-])[O-].[K+].[K+].[OH2:42]>CN(C)C=O>[Cl:26][C:27]1[C:32]([O:42][C:2]2[CH:3]=[CH:4][C:5]([N+:23]([O-:25])=[O:24])=[C:6]([N:8]3[C:13](=[O:14])[N:12]([CH3:15])[C:11](=[O:16])[N:10]([CH2:17][C:18]([O:20][CH3:21])=[O:19])[C:9]3=[O:22])[CH:7]=2)=[C:31]([Cl:34])[CH:30]=[CH:29][C:28]=1[CH3:36]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 873052,4-Dichloro-m-cresolHCID 57274056Methyl 3-(5-fluoro-2-nitrophenyl)tetrahydro-5-methyl-2,4,6-trioxo-s-triazine-1(2H)-acetate

Product 1

HCID 70346684Methyl 3-{5-[(2,4-dichloro-m-tolyl)oxy]-2-nitrophenyl}tetrahydro-5-methyl-2,4,6-trioxo-s-triazine-1(2H)-acetate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of methyl 3-(5-fluoro-2-nitrophenyl)tetrahydro-5-methyl-2,4,6-trioxo-s-triazine-1-(2H)-acetate (0.51 g, 1.4 mmol), 2,4-dichloro-3-methylphenol (0.33 g, 1.9 mmol) and potassium carbonate (0.28 g, 2.0 mmol) in N,N-dimethylformamide is stirred overnight at room temperature and poured into water. The aqueous mixture is extracted with ethyl acetate. The organic extracts are combined, washed sequentially with water, 1M sodium hydroxide solution, water and brine, dried over anhydrous magnesium sulfate and concentrated in vacuo to obtain a yellow solid. The solid is slurried with an ether/hexanes (1:1) solution, filtered and dried in vacuo to give the title product as a yellow solid, mp 199.9°-202° C.

Workup

  1. extractionThe aqueous mixture is extracted with ethyl acetate
  2. washwashed sequentially with water, 1M sodium hydroxide solution, water and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customto obtain a yellow solid
  6. filtrationfiltered
  7. customdried in vacuo

Sources & evidence

ORD record
ord-247de6d87dc3488ca780803d04c4b442
Source dataset
uspto-grants-1996_05
Patent number
US05519133

Reaction notes

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