Sulfuric Acid → HCID 17990189, compound

HRID 2248561Notes

Reaction equation

HRID 2248561 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

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 to neutrality with water and combined with the methanolic solution. This solution is dried over anhydrous sodium sulphate and evaporated to dryness. The crystalline residue is suspended 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
  6. dry with materialThis solution is dried over anhydrous sodium sulphate
  7. customevaporated to dryness
  8. customis suspended with 100 ml of ethyl acetate at 70° C.
  9. filtrationthe crystals are filtered off under suction
  10. washwashed with diethyl ether

Sources & evidence

ORD record
ord-f45f32a67a4b4946a10a32f8f365112f
Source dataset
uspto-grants-1991_08
Patent number
US05041156

Reaction notes

Loading…