Dimethyl Sulfate → HCID 19745820, compound

HRID 2253580Notes

Reaction equation

HRID 2253580 reaction equation
[F:1][C:2]1[C:14]([N:15]2[C:20](=[O:21])[CH:19]=[C:18]([C:22]([F:25])([F:24])[F:23])[NH:17][C:16]2=[O:26])=[CH:13][C:5]2[N:6]([CH2:10][C:11]#[CH:12])[C:7](=[O:9])[S:8][C:4]=2[CH:3]=1.S(OC)(O[CH3:31])(=O)=O.C(=O)([O-])[O-].[Na+].[Na+]>CC(C)=O>[F:1][C:2]1[C:14]([N:15]2[C:20](=[O:21])[CH:19]=[C:18]([C:22]([F:23])([F:24])[F:25])[N:17]=[C:16]2[O:26][CH3:31])=[CH:13][C:5]2[N:6]([CH2:10][C:11]#[CH:12])[C:7](=[O:9])[S:8][C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 6497Dimethyl SulfateHCID 10340Sodium CarbonateHCID 19745774HCID 19745774, compound

Product 1

HCID 19745820HCID 19745820, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 27.50 g of 3-[6-fluoro-2-oxo-3-(2-propynyl)-5-benzothiazolinyl]-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione (see Example 1), 10.80 g of dimethyl sulphate and 9.08 g of sodium carbonate in 250 ml of acetone is heated at the boiling temperature while stirring for 1.5 hours. After cooling the solid constituent is filtered off under suction and washed with acetone. The filtrate is then evaporated to dryness under reduced pressure, the residue is dissolved in 350 ml of ethyl acetate and the solution is washed three times with 300 ml of water each time. Subsequently, the organic phase is dried over anhydrous sodium sulphate and evaporated to dryness under reduced pressure, and the resinous residue is purified by chromatography on 1.5 g of silica gel using ethyl acetate/n-hexane (1:3) as the eluent. The first fraction is recrystallized from ethyl acetate/diethyl ether (1:1), whereby there is obtained 6-fluoro-5-[2-methoxy-6-oxo-4-trifluoromethyl-1(6H)-pyrimidinyl]-3-(2-propynyl)-2-benzothiazolinone, m.p. 191°-192° C. The 2nd fraction is recrystallized from diethyl ether/n-hexane (1:1) and there is thus obtained 3-[6-fluoro-2-oxo-3-(2-propynyl)-5-benzothiazolinyl]-1-methyl-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione, m.p. 190°-192° C.

Workup

  1. temperatureis heated at the boiling temperature
  2. temperatureAfter cooling the solid constituent
  3. filtrationis filtered off under suction
  4. washwashed with acetone
  5. customThe filtrate is then evaporated to dryness under reduced pressure
  6. dissolutionthe residue is dissolved in 350 ml of ethyl acetate
  7. washthe solution is washed three times with 300 ml of water each time
  8. dry with materialSubsequently, the organic phase is dried over anhydrous sodium sulphate
  9. customevaporated to dryness under reduced pressure
  10. customthe resinous residue is purified by chromatography on 1.5 g of silica gel
  11. customThe first fraction is recrystallized from ethyl acetate/diethyl ether (1:1)

Sources & evidence

ORD record
ord-8e804971be6f4a369a59bf58d2444833
Source dataset
uspto-grants-1993_08
Patent number
US05232898

Reaction notes

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