Sulfuryl chloride → HCID 20130619, compound

HRID 845951Notes

Reaction equation

HRID 845951 reaction equation
S(Cl)([Cl:4])(=O)=O.[Cl:6][C:7]1[CH:18]=[C:17]([F:19])[C:16]([N:20]2[C:25](=[O:26])[CH:24]=[C:23]([CH3:27])[N:22]([CH3:28])[C:21]2=[O:29])=[CH:15][C:8]=1[C:9]([O:11][CH:12]([CH3:14])[CH3:13])=[O:10]>C(O)(=O)C>[Cl:6][C:7]1[CH:18]=[C:17]([F:19])[C:16]([N:20]2[C:25](=[O:26])[C:24]([Cl:4])=[C:23]([CH3:27])[N:22]([CH3:28])[C:21]2=[O:29])=[CH:15][C:8]=1[C:9]([O:11][CH:12]([CH3:14])[CH3:13])=[O:10]

Participants

4

Reactant 2

HCID 24648Sulfuryl chlorideHCID 19832675HCID 19832675, compound

Product 1

HCID 20130619HCID 20130619, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

6.3 g of sulphuryl chloride are added dropwise with stirring to a solution of 15.0 g of isopropyl 2-chloro-4-fluoro-5-[3,6-dihydro-3,4-dimethyl-2,6-dioxo-1(2H)-pyrimidinyl]-benzoate in 100 ml of acetic acid at room temperature during 1 minute, during which the temperature rises to approx. 30° C. Then the reaction mixture is stirred for a further 15 minutes at room temperature and evaporated to dryness under reduced pressure. The residue is dissolved in ethyl acetate and the solution washed in turn with aqueous sodium bicarbonate solution and water. The organic phase is dried over anhydrous sodium sulphate and evaporated to dryness. The residue is recrystallized from methylene chloride/diethyl ether. Isopropyl 2-chloro-4-fluoro-5-[5-chloro-3,6-dihydro-3,4-dimethyl-2,6-dioxo-1(2H)-pyrimidinyl]-benzoate, m.p. 150°-153° C., is obtained.

Workup

  1. customrises to approx. 30° C
  2. customevaporated to dryness under reduced pressure
  3. dissolutionThe residue is dissolved in ethyl acetate
  4. washthe solution washed in turn with aqueous sodium bicarbonate solution and water
  5. dry with materialThe organic phase is dried over anhydrous sodium sulphate
  6. customevaporated to dryness
  7. customThe residue is recrystallized from methylene chloride/diethyl ether

Sources & evidence

ORD record
ord-e004e99939eb4e6c8dd0a22e896a3b5e
Source dataset
uspto-grants-1988_07
Patent number
US04760163

Reaction notes

Loading…