Diethyl Ether → HCID 54333796, compound

HRID 1274553Notes

Reaction equation

HRID 1274553 reaction equation
[C:1]([O:5][CH3:6])(=[O:4])[CH2:2][SH:3].Br[CH2:8][C:9]1[C:13]2[CH:14]=[C:15]([N:18]3[C:23](=[O:24])[CH:22]=[C:21]([C:25]([F:28])([F:27])[F:26])[N:20]([CH3:29])[C:19]3=[O:30])[CH:16]=[CH:17][C:12]=2[S:11][N:10]=1.C(OCC)C>O1CCCC1.C(Cl)Cl.O>[CH3:6][O:5][C:1](=[O:4])[CH2:2][S:3][CH2:8][C:9]1[C:13]2[CH:14]=[C:15]([N:18]3[C:23](=[O:24])[CH:22]=[C:21]([C:25]([F:28])([F:27])[F:26])[N:20]([CH3:29])[C:19]3=[O:30])[CH:16]=[CH:17][C:12]=2[S:11][N:10]=1

Participants

7

Reactant 3

HCID 3283Diethyl EtherHCID 16907Methyl ThioglycolateHCID 22119928HCID 22119928, compound

Product 1

HCID 54333796HCID 54333796, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of hexanes washed sodium hydride (0.0360 g of a 60% dispersion in oil, 0.900 mmol) in tetrahydrofuran is treated with methyl thioglycolate (90.0 mL, 1.00 mmol), stirred until gas evolution stops, treated dropwise with a solution of 3-[3-(bromomethyl)-1,2-benzisothiazol-5-yl]-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione (0.300 g, 0.710 mmol) in tetrahydrofuran, stirred for 10 minutes, and concentrated in vacuo to obtain a residue. The residue is diluted with methylene chloride and water. The organic phase is separated, dried over anhydrous magnesium sulfate, and concentrated in vacuo to obtain an oil. Column chromatography of the oil using silica gel and a 5% diethyl ether in methylene chloride solution gives the title product as a clear oil which is identified by 1H NMR spectral analysis.

Workup

  1. washwashed sodium hydride (0.0360 g of a 60% dispersion in oil, 0.900 mmol) in tetrahydrofuran
  2. stirringstirred for 10 minutes
  3. concentrationconcentrated in vacuo
  4. customto obtain a residue
  5. customThe organic phase is separated
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated in vacuo
  8. customto obtain an oil

Sources & evidence

ORD record
ord-7a7bc83adc1b48a5a5eb6930318a5fdc
Source dataset
uspto-grants-2000_12
Patent number
US06156700

Reaction notes

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