Diethyl Ether → HCID 22119947, compound

HRID 1274554Notes

Reaction equation

HRID 1274554 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.[CH3:25][S-:26].[Na+].C(OCC)C>C(#N)C.C(Cl)Cl.O>[CH3:23][N:14]1[C:15]([C:19]([F:22])([F:21])[F:20])=[CH:16][C:17](=[O:18])[N:12]([C:9]2[CH:10]=[CH:11][C:6]3[S:5][N:4]=[C:3]([CH2:2][S:26][CH3:25])[C:7]=3[CH:8]=2)[C:13]1=[O:24]

Participants

7

Reactant 3

HCID 3283Diethyl EtherHCID 4378561Sodium methanethiolate2×HCID 22119928HCID 22119928, compound

Product 1

HCID 22119947HCID 22119947, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent2×

Procedure

A solution of 3-[3-(bromomethyl)-1,2-benzisothiazol-5-yl]-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione (1.66 g, 3.95 mmol) in acetonitrile is treated with sodium thiomethoxide (0.332 g, 4.74 mmol), stirred overnight at room temperature, treated with additional sodium thiomethoxide (about 15 mg), stirred for one hour, and concentrated in vacuo to obtain a residue. The residue is diluted with methylene chloride and water. The organic phase is separated, washed with brine, dried over anhydrous magnesium sulfate, and concentrated in vacuo to obtain a solid. Column chromatography of the solid using silica gel and a 2% diethyl ether in methylene chloride solution gives the title product as a white solid which is identified by 1H NMR spectral analysis.

Workup

  1. stirringstirred for one hour
  2. concentrationconcentrated in vacuo
  3. customto obtain a residue
  4. customThe organic phase is separated
  5. washwashed with brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated in vacuo
  8. customto obtain a solid

Sources & evidence

ORD record
ord-8fef16ee63a1447086868400ae50802f
Source dataset
uspto-grants-2000_12
Patent number
US06156700

Reaction notes

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