Sulfuric Acid → HCID 17990189, compound

HRID 2165804Notes

Reaction equation

HRID 2165804 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]([CH:23]([F:25])[F:24])[C:16]2=[O:26])=[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]([CH3:22])[N:17]([CH:23]([F:24])[F:25])[C:16]2=[O:26])=[CH:10][C:3]=1[C:4]([OH:6])=[O:5]

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 135408Benzoic acid, 2-chloro-5-(3-(difluoromethyl)-3,6-dihydro-4-methyl-2,6-dioxo-1(2H)-pyrimidinyl)-4-fluoro-, 1-methylethyl ester

Product 1

HCID 17990189HCID 17990189, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
70 °C

Procedure

A solution of 18.0 g of isopropyl 2-chloro-5-[3-difluoromethyl-3,6-dihydro-4-methyl-2,6-dioxo-1(2H)-pyrimidinyl]- 4-fluorobenzoate in 60 ml of methylene chloride is stirred intensively for 5 minutes with 100 ml of concentrated sulphuric acid and subsequently poured onto 1 kg of ice. The resulting crystals are filtered off under suction. washed twice with 50 ml of water each time and dissolved in 300 ml of methanol. The mother liquor is extracted twice with 100 ml of methylene chloride each time and the organic phase is washed with water to neutrality and combined with the methanolic solution. This solution is dried over anhydrous sodium sulphate and evaporated to dryness. The crystalline residue is stirred with 100 ml of ethyl acetate at 70° C. and cooled to room temperature, and the crystals are filtered off under suction and washed with diethyl ether. There is obtained 2-chloro-5-[3 -difluoromethyl-3.6-dihydro-4-methyl- 2,6-dioxo-1(2H)-pyrimidinyl]-4-fluorobenzoic acid, m.p. 247°-248° C.

Workup

  1. filtrationThe resulting crystals are filtered off under suction
  2. washwashed twice with 50 ml of water each time
  3. dissolutiondissolved in 300 ml of methanol
  4. extractionThe mother liquor is extracted twice with 100 ml of methylene chloride each time
  5. washthe organic phase is washed with water to neutrality
  6. dry with materialThis solution is dried over anhydrous sodium sulphate
  7. customevaporated to dryness
  8. temperaturecooled to room temperature
  9. filtrationthe crystals are filtered off under suction
  10. washwashed with diethyl ether

Sources & evidence

ORD record
ord-b90e415ef4144f2385e66158992014f8
Source dataset
uspto-grants-1990_07
Patent number
US04941909

Reaction notes

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