Sulfuric Acid → 2-chloro-4-fluoro-5-[2-methoxy-6-oxo-4-trifluoromethyl-1(6H)-pyrimidinyl]-benzoic acid

HRID 2248560Notes

Reaction equation

HRID 2248560 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]([C:22]([F:25])([F:24])[F:23])[N:17]=[C:16]2[O:26][CH3:27])=[CH:10][C:3]=1[C:4]([O:6]C(C)C)=[O:5].S(=O)(=O)(O)O>C(Cl)Cl>[Cl:1][C:2]1[CH:13]=[C:12]([F:14])[C:11]([N:15]2[C:20](=[O:21])[CH:19]=[C:18]([C:22]([F:23])([F:25])[F:24])[N:17]=[C:16]2[O:26][CH3:27])=[CH:10][C:3]=1[C:4]([OH:6])=[O:5]

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 197808272-chloro-4-fluoro-5-[2-methoxy-6-oxo-4-trifluoromethyl-1(6H)-pyrimidinyl]-benzoic 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 while stirring and cooling at 20°-25° C. with 25 ml of concentrated sulphuric acid. The reaction mixture is stirred at room temperature for 20 minutes and poured onto 100 g of ice. The orqanic 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. Subsequently, the solution is 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. stirringThe reaction mixture is stirred at room temperature for 20 minutes
  2. customThe orqanic phase is separated
  3. extractionthe aqueous phase is extracted twice with 15 ml of ethyl acetate each time
  4. washthe combined organic phases are washed
  5. dry with materialSubsequently, the solution is dried over anhydrous sodium sulphate
  6. customevaporated to dryness under reduced pressure
  7. customThe resinous residue is recrystallized from diethyl ether/ n-hexane

Sources & evidence

ORD record
ord-df89e10e7f7a40a48fc00d3a4455d154
Source dataset
uspto-grants-1991_08
Patent number
US05041156

Reaction notes

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