Hydrochloric Acid → HCID 20025989, compound

HRID 1722977Notes

Reaction equation

HRID 1722977 reaction equation
[Cl:1][C:2]1[CH:15]=[C:14]([F:16])[C:13]([N:17]2[C:22](=[O:23])[CH:21]=[C:20]([C:24]([F:27])([F:26])[F:25])[N:19]([CH3:28])[C:18]2=[O:29])=[CH:12][C:3]=1[O:4][CH2:5][CH2:6][NH:7]C(=O)CC.Cl>C(O)C.O>[ClH:1].[NH2:7][CH2:6][CH2:5][O:4][C:3]1[C:2]([Cl:1])=[CH:15][C:14]([F:16])=[C:13]([N:17]2[C:22](=[O:23])[CH:21]=[C:20]([C:24]([F:25])([F:26])[F:27])[N:19]([CH3:28])[C:18]2=[O:29])[CH:12]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 20025992HCID 20025992, compound

Product 1

HCID 20025989HCID 20025989, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A solution of 17.0 g of N-[2-{2-chloro-5-[3,6-dihydro-2,6-dioxo-3-methyl-4 -trifluoromethyl-1(2H)-pyrimidinyl]-4-fluorophenoxy}-ethyl]propionamide in 100 ml of ethanol is heated at reflux temperature for 5 hours with a solution of 75 ml of concentrated hydrochloric acid in 75 ml of water. The ethanol is subsequently distilled off at 50° C. and the clear aqueous solution is neutralized with sodium bicarbonate. The oily precipitate is dissolved in ethyl acetate and the solution is washed with water, dried over anhydrous sodium sulphate and evaporated to dryness under reduced pressure. The resinous residue is dissolved in 200 ml of 2N hydrochloric acid at 50° C., the mixture is extracted with a small amount of ethyl acetate and the aqueous phase is evaporated under reduced pressure until crystallization occurs. 50 ml of diethyl ether are subsequently added and the mixture is stirred. The crystals are filtered off under suction, washed with diethyl ether and dried at 50° C. in a vacuum. There is obtained 3-[5-(2-aminoethoxy)-4-chloro-2-fluorophenyl]-1-methyl-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione hydrochloride, m.p. 217°-227° C. (decomposition).

Workup

  1. distillationThe ethanol is subsequently distilled off at 50° C.
  2. dissolutionThe oily precipitate is dissolved in ethyl acetate
  3. washthe solution is washed with water
  4. dry with materialdried over anhydrous sodium sulphate
  5. customevaporated to dryness under reduced pressure
  6. dissolutionThe resinous residue is dissolved in 200 ml of 2N hydrochloric acid at 50° C.
  7. extractionthe mixture is extracted with a small amount of ethyl acetate
  8. customthe aqueous phase is evaporated under reduced pressure until crystallization
  9. addition50 ml of diethyl ether are subsequently added
  10. filtrationThe crystals are filtered off under suction
  11. washwashed with diethyl ether
  12. customdried at 50° C. in a vacuum

Sources & evidence

ORD record
ord-971594d5141542a38fcd30e708dcbb1b
Source dataset
uspto-grants-1989_08
Patent number
US04859229

Reaction notes

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