Nitric Acid → HCID 20130709, compound

HRID 845960Notes

Reaction equation

HRID 845960 reaction equation
[Cl:1][C:2]1[CH:13]=[C:12]([F:14])[C:11]([N:15]2[C:20](=[O:21])[CH:19]=[C:18]([CH3:22])[NH:17][C:16]2=[O:23])=[CH:10][C:3]=1[C:4]([O:6][CH:7]([CH3:9])[CH3:8])=[O:5].[N+:24]([O-])([OH:26])=[O:25]>C(Cl)Cl.S(=O)(=O)(O)O.C(OCC)(=O)C>[Cl:1][C:2]1[CH:13]=[C:12]([F:14])[C:11]([N:15]2[C:20](=[O:21])[C:19]([N+:24]([O-:26])=[O:25])=[C:18]([CH3:22])[NH:17][C:16]2=[O:23])=[CH:10][C:3]=1[C:4]([O:6][CH:7]([CH3:9])[CH3:8])=[O:5]

Participants

6

Reactant 2

HCID 944Nitric AcidHCID 19994231HCID 19994231, compound

Product 1

HCID 20130709HCID 20130709, compound

Reagents, catalysts & solvents 3

HCID 1118Sulfuric AcidCatalystHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 1.50 g of isopropyl 2-chloro-4-fluoro-5-[3,6-dihydro-4methyl-2,6-dioxo-1-(2H)-pyrimidinyl]-benzoate in 30 ml of methylene chloride at room temperature is treated with stirring with 2.0 ml of 100% nitric acid. The solution is then treated with 5 drops of concentrated sulphuric acid and stirred for 48 hours at room temperature. The reaction mixture is poured into 150 ml of ice/water, diluted with 100 ml of ethyl acetate and washed four times with 150 ml of water. The organic phase is dried over anhydrous sodium sulphate and evaporated to dryness under reduced pressure. The residue is recrystallized from diethyl ether. Isopropyl 2-chloro-4-fluoro-5-[3,6-dihydro-4-methyl-5-nitro-2,6-dioxo-1(2H)-pyrimidinyl]-benzoate, m.p. 202°-205° C., is obtained.

Workup

  1. washwashed four times with 150 ml of water
  2. dry with materialThe organic phase is dried over anhydrous sodium sulphate
  3. customevaporated to dryness under reduced pressure
  4. customThe residue is recrystallized from diethyl ether

Sources & evidence

ORD record
ord-1615df16fcc34949b3c419e7d24f8468
Source dataset
uspto-grants-1988_07
Patent number
US04760163

Reaction notes

Loading…