Hydrochloric Acid → HCID 19912192, compound

HRID 1090976Notes

Reaction equation

HRID 1090976 reaction equation
O1CCOCC1.[CH2:7]([S:9]([N:12](S(CC)(=O)=O)[C:13]1[C:14]([Cl:33])=[CH:15][C:16]([Cl:32])=[C:17]([N:19]2[C:24](=[O:25])[CH:23]=[C:22]([C:26]([F:29])([F:28])[F:27])[N:21]([CH3:30])[C:20]2=[O:31])[CH:18]=1)(=[O:11])=[O:10])[CH3:8].[OH-].[Na+].Cl>O>[Cl:32][C:16]1[CH:15]=[C:14]([Cl:33])[C:13]([NH:12][S:9]([CH2:7][CH3:8])(=[O:10])=[O:11])=[CH:18][C:17]=1[N:19]1[C:24](=[O:25])[CH:23]=[C:22]([C:26]([F:28])([F:27])[F:29])[N:21]([CH3:30])[C:20]1=[O:31]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 312751,4-DioxaneHCID 19912194HCID 19912194, compound

Product 1

HCID 19912192HCID 19912192, compoundYield 69.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 8 ml of dioxane, 0.80 g of the obtained 3-[5-bis(ethanesulfonyl)amino-2,4-dichlorophenyl]-1-methyl-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione was dissolved and 0.12 g of sodium hydroxide (93%) and 2 ml of water were added to the obtained solution After the mixed solution was stirred for 4 hours, a dilute hydrochloric acid was added thereto in order to acidify the resultant solution. The reaction mixture was extracted with ethyl acetate. The obtained extract of the ethyl acetate layer was washed with water and a saturated sodium chloride aqueous solution, and dried over anhydrous sodium sulfate. Then ethyl acetate was distilled off to obtain a crude product. The obtained product was purified by preparative thin-layer chromatography (developing solvent: hexane/ethyl acetate =3/2) to obtain 0.46 g of the objective product as white crystals.

Workup

  1. extractionThe reaction mixture was extracted with ethyl acetate
  2. extractionThe obtained extract of the ethyl acetate layer
  3. washwas washed with water
  4. dry with materiala saturated sodium chloride aqueous solution, and dried over anhydrous sodium sulfate
  5. distillationThen ethyl acetate was distilled off
  6. customto obtain a crude product
  7. customThe obtained product was purified by preparative thin-layer chromatography (developing solvent: hexane/ethyl acetate =3/2)

Sources & evidence

ORD record
ord-168d30248ba1480b9d1d6eea8befa8d0
Source dataset
uspto-grants-1992_01
Patent number
US05084084

Reaction notes

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