Sulfuric Acid → HCID 21270742, compound

HRID 1193925Notes

Reaction equation

HRID 1193925 reaction equation
S(=O)(=O)(O)O.[Cl:6][C:7]1[C:12]([O:13]C(C)C)=[CH:11][C:10]([N:17]2[C:22](=[O:23])[CH:21]=[C:20]([C:24]([F:27])([F:26])[F:25])[N:19]=[C:18]2[O:28][CH3:29])=[C:9]([F:30])[CH:8]=1>C(Cl)Cl>[Cl:6][C:7]1[C:12]([OH:13])=[CH:11][C:10]([N:17]2[C:22](=[O:23])[CH:21]=[C:20]([C:24]([F:25])([F:27])[F:26])[N:19]=[C:18]2[O:28][CH3:29])=[C:9]([F:30])[CH:8]=1

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 21270755HCID 21270755, compound

Product 1

HCID 21270742HCID 21270742, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3.70 ml of concentrated sulphuric acid are added dropwise during 1 minute to a solution of 3.80 g of 1-(4-chloro-2-fluoro-5-isopropoxyphenyl) -2-methoxy-4-trifluoromethyl-6(1H)-pyrimidinone (see Example 4, 2nd part) in 10 ml of methylene chloride while stirring and cooling at room temperature. The reaction mixture is stirred at room temperature for 3 hours and poured on to 15 g of ice. The organic phase is separated and the aqueous phase is extracted twice with 5 ml of methylene chloride each time and the combined organic phases are washed twice with 10 ml of water each time. The methylene chloride solution is subsequently dried over anhydrous sodium sulphate and evaporated to dryness under reduced pressure. The residue is recrystallized from diethyl ether/n-hexane. There is obtained 1-(4-chloro-2-fluoro-5-hydroxyphenyl)-2-methoxy-4-trifluoromethyl-6(1H)-pyrimidinone, m.p. 147°-149° C.

Workup

  1. stirringThe reaction mixture is stirred at room temperature for 3 hours
  2. customThe organic phase is separated
  3. extractionthe aqueous phase is extracted twice with 5 ml of methylene chloride each time
  4. washthe combined organic phases are washed twice with 10 ml of water each time
  5. dry with materialThe methylene chloride solution is subsequently dried over anhydrous sodium sulphate
  6. customevaporated to dryness under reduced pressure
  7. customThe residue is recrystallized from diethyl ether/n-hexane

Sources & evidence

ORD record
ord-89e615260db2412a91bfd49078a0fd5c
Source dataset
uspto-grants-1989_03
Patent number
US04812164

Reaction notes

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