Pyridine → methyl 3-(5-fluoro-2-nitrophenyl)tetrahydro-2,4,6-trioxo-s-triazine-1(2H)-acetate

HRID 2255876Notes

Reaction equation

HRID 2255876 reaction equation
[CH3:1][O:2][C:3](=[O:19])[CH2:4][NH:5][C:6](=[O:18])[NH:7][C:8]1[CH:13]=[C:12]([F:14])[CH:11]=[CH:10][C:9]=1[N+:15]([O-:17])=[O:16].[C:20](=[O:25])=[N:21][C:22](Cl)=[O:23].N1C=CC=CC=1>C(Cl)Cl>[F:14][C:12]1[CH:11]=[CH:10][C:9]([N+:15]([O-:17])=[O:16])=[C:8]([N:7]2[C:22](=[O:23])[NH:21][C:20](=[O:25])[N:5]([CH2:4][C:3]([O:2][CH3:1])=[O:19])[C:6]2=[O:18])[CH:13]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 119708Isocyanatocarbonyl chlorideHCID 53945193N-[(5-Fluoro-2-nitrophenyl)carbamoyl]glycine methyl ester

Product 1

HCID 11067766methyl 3-(5-fluoro-2-nitrophenyl)tetrahydro-2,4,6-trioxo-s-triazine-1(2H)-acetate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of N-[(5-fluoro-2-nitrophenyl)carbamoyl]glycine methyl ester (20.47 g, 75.46 mmol) in methylene chloride is cooled in an ice-bath, treated with N-(chlorocarbonyl) isocyanate (7 mL, 86.94 mmol), treated dropwise with pyridine (7.5 mL, 92.92 mmol), warmed to and stirred at room temperature for 90 minutes, and filtered. The filtrate is poured into 0.11M hydrochloric acid (450 mL), the phases are separated and the aqueous phase is extracted with methylene chloride. The organic phase and extracts are combined, washed with brine, dried over anhydrous magnesium sulfate and concentrated in vacuo to obtain the title product as a yellow solid.

Workup

  1. temperaturewarmed to and
  2. filtrationfiltered
  3. additionThe filtrate is poured into 0.11M hydrochloric acid (450 mL)
  4. customthe phases are separated
  5. extractionthe aqueous phase is extracted with methylene chloride
  6. washwashed with brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ac3399a1deae4c1783482834d58596e6
Source dataset
uspto-grants-1997_08
Patent number
US05654256

Reaction notes

Loading…