Sulfuric Acid → Benzoic Acid

HRID 1193942Notes

Reaction equation

HRID 1193942 reaction equation
Cl[C:2]1[CH:13]=[C:12](F)[C:11](N2C(=O)C=C(C(F)(F)F)N=C2OC)=[CH:10][C:3]=1[C:4]([O:6]C(C)C)=[O:5].S(=O)(=O)(O)O>C(Cl)Cl>[C:4]([OH:6])(=[O:5])[C:3]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:2]=1

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 19994237isopropyl 2-chloro-4-fluoro-5-[2-methoxy-6-oxo-4-trifluoromethyl-1(6H)-pyrimidinyl]-benzoate

Product 1

HCID 243Benzoic Acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 5 g of isopropyl 2-chloro-4-fluoro-5-[2-methoxy-6-oxo-4-trifluoromethyl-1(6H)-pyrimidinyl]-benzoate in 20 ml of methylene chloride is treated with 25 ml of concentrated sulphuric acid while stirring and cooling at 20°-25° C. The reaction mixture is stirred at room temperature for 20 minutes and poured onto 100 g of ice. The organic phase is separated, the aqueous phase is extracted twice with 15 ml of ethyl acetate each time and the combined organic phases are washed to neutrality with water. The solution is subsequently dried over anhydrous sodium sulphate and evaporated to dryness under reduced pressure. The resinous residue is recrystallized from diethyl ether/n-hexane. There is obtained 2-chloro-4-fluoro-5-[2-methoxy-6-oxo-4-trifluoromethyl-1(6H)-pyrimidinyl[-benzoic acid, m.p. 205°-210° C.

Workup

  1. temperaturecooling at 20°-25° C
  2. stirringThe reaction mixture is stirred at room temperature for 20 minutes
  3. customThe organic phase is separated
  4. extractionthe aqueous phase is extracted twice with 15 ml of ethyl acetate each time
  5. washthe combined organic phases are washed
  6. dry with materialThe solution is subsequently dried over anhydrous sodium sulphate
  7. customevaporated to dryness under reduced pressure
  8. customThe resinous residue is recrystallized from diethyl ether/n-hexane

Sources & evidence

ORD record
ord-b1c637fdca754012aad2892134a2316d
Source dataset
uspto-grants-1989_03
Patent number
US04812164

Reaction notes

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