Diethyl Ether → HCID 22119983, compound

HRID 1274606Notes

Reaction equation

HRID 1274606 reaction equation
Br[CH2:2][C:3]1[C:7]2[CH:8]=[C:9]([N:12]3[C:17](=[O:18])[CH:16]=[C:15]([C:19]([F:22])([F:21])[F:20])[N:14]([CH3:23])[C:13]3=[O:24])[CH:10]=[CH:11][C:6]=2[S:5][N:4]=1.[F-:25].C([N+](CCCC)(CCCC)CCCC)CCC.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(OCC)C>O1CCCC1.C(Cl)Cl>[F:25][CH2:2][C:3]1[C:7]2[CH:8]=[C:9]([N:12]3[C:17](=[O:18])[CH:16]=[C:15]([C:19]([F:22])([F:21])[F:20])[N:14]([CH3:23])[C:13]3=[O:24])[CH:10]=[CH:11][C:6]=2[S:5][N:4]=1

Participants

7

Reactant 4

HCID 3283Diethyl EtherHCID 6101p-Toluenesulfonic acidHCID 2724141Tetrabutylammonium FluorideHCID 22119928HCID 22119928, compound

Product 1

HCID 22119983HCID 22119983, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 3-[3-(bromomethyl)-1,2-benzisothiazol-5-yl]-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione (1.00 g, 0.00240 mol), 14.4 mL of a 1 M tetrabutylammonium fluoride in tetrahydrofuran solution (0.0144 mol) and anhydrous p-toluenesulfonic acid (1.36 g, 0.00790 mol) in tetrahydrofuran is stirred at room temperature for 30 minutes, refluxed for three hours, stirred at room temperature for three days, refluxed for 22 hours, partially concentrated in vacuo, and diluted with ethyl acetate. The resultant mixture is washed sequentially with water and brine, dried over anhydrous magnesium sulfate, and concentrated in vacuo to obtain an orange solid. Column chromatography of the solid using silica gel and a 2.5% diethyl ether in methylene chloride solution gives the title product as a white solid (0.42 g, mp 201-202° C.).

Workup

  1. temperaturerefluxed for three hours
  2. temperaturerefluxed for 22 hours
  3. concentrationpartially concentrated in vacuo
  4. additiondiluted with ethyl acetate
  5. washThe resultant mixture is washed sequentially with water and brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated in vacuo
  8. customto obtain an orange solid

Sources & evidence

ORD record
ord-4aa9981b1d7743c9be9c34b686e29883
Source dataset
uspto-grants-2000_12
Patent number
US06156700

Reaction notes

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