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 1451174Notes

Reaction equation

HRID 1451174 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, M 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, M 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-86433f95f69c4659acab20a7a1e66752
Source dataset
uspto-grants-1997_02
Patent number
US05604180

Reaction notes

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