HCID 19745792, compound → HCID 19745785, compound

HRID 2253583Notes

Reaction equation

HRID 2253583 reaction equation
[CH3:1][N:2]1[C:7]([CH3:8])=[CH:6][C:5](=[O:9])[N:4]([C:10]2[C:11]([F:23])=[CH:12][C:13]3[S:17][C:16](=[O:18])[N:15](C(C)C)[C:14]=3[CH:22]=2)[C:3]1=[O:24]>S(=O)(=O)(O)O>[CH3:1][N:2]1[C:7]([CH3:8])=[CH:6][C:5](=[O:9])[N:4]([C:10]2[C:11]([F:23])=[CH:12][C:13]3[S:17][C:16](=[O:18])[NH:15][C:14]=3[CH:22]=2)[C:3]1=[O:24]

Participants

3

Reactant 1

HCID 19745792HCID 19745792, compound

Product 1

HCID 19745785HCID 19745785, compound

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
150 °C

Procedure

34.94 g of 1,6-dimethyl-3-(6-fluoro-3-isopropyl-2-oxo-5-benzothiazolinyl)-2,4(1H,3H)-pyrimidinedione (see Example 49) are dissolved in 200 ml of concentrated sulphuric acid while stirring and gassing with nitrogen and the solution is heated to 150° C. for 45 minutes. The reaction mixture is cooled to 25° C. and poured on to 1 kg of ice, and the precipitated product is filtered off under suction and washed neutral with water. The filter cake is suspended in 500 ml of ethyl acetate at 60° C., the suspension is concentrated to 250 ml, the product, after cooling, is filtered off under suction, the filtrate is back-washed with ethyl acetate and dried at 50° C. under reduced pressure. In this manner there is obtained 1,6-dimethyl-3-(6-fluoro-2-oxo-5-benzothiazolinyl)-2,4-(1H,3H)-pyrimidinedione, m.p.>250° C.

Workup

  1. temperatureThe reaction mixture is cooled to 25° C.
  2. filtrationthe precipitated product is filtered off under suction
  3. washwashed neutral with water
  4. customis suspended in 500 ml of ethyl acetate at 60° C.
  5. concentrationthe suspension is concentrated to 250 ml
  6. temperaturethe product, after cooling
  7. filtrationis filtered off under suction
  8. washthe filtrate is back-washed with ethyl acetate
  9. customdried at 50° C. under reduced pressure

Sources & evidence

ORD record
ord-4737dd476d1f4c42bae88afaf1c6aba6
Source dataset
uspto-grants-1993_08
Patent number
US05232898

Reaction notes

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