Nitric Acid → 1-(2-Chloro-4-fluoro-5-nitrophenyl)-3-methyl-s-triazine-2,4,6(1H,3H,5H)-trione

HRID 975760

Reaction equation

HRID 975760 reaction equation
[N+:1]([O-:4])(O)=[O:2].[Cl:5][C:6]1[CH:11]=[C:10]([F:12])[CH:9]=[CH:8][C:7]=1[N:13]1[C:18](=[O:19])[NH:17][C:16](=[O:20])[N:15]([CH3:21])[C:14]1=[O:22]>S(=O)(=O)(O)O>[Cl:5][C:6]1[CH:11]=[C:10]([F:12])[C:9]([N+:1]([O-:4])=[O:2])=[CH:8][C:7]=1[N:13]1[C:18](=[O:19])[NH:17][C:16](=[O:20])[N:15]([CH3:21])[C:14]1=[O:22]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 572686601-(2-chloro-4-fluorophenyl)-3-methyl-s-triazine-2,4,6(1H,3H,5H)-trione

Product 1

HCID 572803321-(2-Chloro-4-fluoro-5-nitrophenyl)-3-methyl-s-triazine-2,4,6(1H,3H,5H)-trioneYield 75.6%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

Nitric acid (70% real, 8.3 mL, 0.131 mol) is added to a solution of 1-(2-chloro-4-fluorophenyl)-3-methyl-s-triazine-2,4,6(1H,3H,5H)-trione (32.4 g, 0.119 mol) in concentrated sulfuric acid while maintaining the reaction mixture temperature below 10° C. After the addition is complete, the reaction mixture is stirred at room temperature for 30 minutes, cooled to 10° C. and diluted with ice-water. The resultant aqueous mixture is filtered to obtain a solid which is washed with water and air-dried to give the title product as a white solid (28.5 g, mp 135°-139° C.).

Workup

  1. temperaturewhile maintaining the reaction mixture temperature below 10° C
  2. additionAfter the addition
  3. temperaturecooled to 10° C.
  4. filtrationThe resultant aqueous mixture is filtered
  5. customto obtain a solid which
  6. washis washed with water
  7. customair-dried

Sources & evidence

ORD record
ord-ab23e1b0547047b2b1832a8329b2bcef
Source dataset
uspto-grants-1997_03
Patent number
US05610120

Linked notes

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