Iodine → HCID 20130614, compound

HRID 845953Notes

Reaction equation

HRID 845953 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])[N:17]([CH3:23])[C:16]2=[O:24])=[CH:10][C:3]=1[C:4]([O:6][CH:7]([CH3:9])[CH3:8])=[O:5].[I:25]I.[N+]([O-])(O)=O>C(O)(=O)C>[Cl:1][C:2]1[CH:13]=[C:12]([F:14])[C:11]([N:15]2[C:20](=[O:21])[C:19]([I:25])=[C:18]([CH3:22])[N:17]([CH3:23])[C:16]2=[O:24])=[CH:10][C:3]=1[C:4]([O:6][CH:7]([CH3:9])[CH3:8])=[O:5]

Participants

5

Reactant 3

HCID 807IodineHCID 944Nitric AcidHCID 19832675HCID 19832675, compound

Product 1

HCID 20130614HCID 20130614, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

1.50 g of isopropyl 2-chloro-4-fluoro-5-[3,6-dihydro-3,4-dimethyl-2,6-dioxo-1(2H)-pyrimidinyl]-benzoate in 10 ml of acetic acid are treated with 0.70 g of iodine and the reaction mixture is stirred for 1 hour at room temperature. Subsequently the reaction mixture is treated with 0.67 g of 100% nitric acid and stirred at room temperature for 3 hours. The reaction mixture is poured into 150 ml of ice/water and extracted with 100 ml of ethyl acetate. The organic phase is washed with 150 ml of water, thereafter with 150 ml of aqueous sodium bicarbonate solution and finally with 150 ml of saturated aqueous sodium bisulphite solution. The upper phase is dried over anhydrous sodium sulphate and evaporated to dryness under reduced pressure. The residue is recrystallized from methylene chloride/n-hexane. Isopropyl 2-chloro-4-fluoro-5-[3,6-dihydro-3,4-dimethyl-5-iodo-2,6-dioxo-1(2H)-pyrimidinyl]-benzoate, m.p. 147°-150° C., is obtained.

Workup

  1. stirringstirred at room temperature for 3 hours
  2. extractionextracted with 100 ml of ethyl acetate
  3. washThe organic phase is washed with 150 ml of water
  4. dry with materialThe upper phase is dried over anhydrous sodium sulphate
  5. customevaporated to dryness under reduced pressure
  6. customThe residue is recrystallized from methylene chloride/n-hexane

Sources & evidence

ORD record
ord-6aae0f8f52534fbb85d283a62475c77a
Source dataset
uspto-grants-1988_07
Patent number
US04760163

Reaction notes

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