Sodium hydride → 3-[3-(4-Isopropyl-2-oxazolin-2-yl)-1,2-benzisothiazol-5-yl]-1-methyl-6-(trifluoromethyl)uracil

HRID 48987Notes

Reaction equation

HRID 48987 reaction equation
Cl[CH2:2][CH:3]([NH:7][C:8]([C:10]1[C:14]2[CH:15]=[C:16]([N:19]3[C:24](=[O:25])[CH:23]=[C:22]([C:26]([F:29])([F:28])[F:27])[N:21]([CH3:30])[C:20]3=[O:31])[CH:17]=[CH:18][C:13]=2[S:12][N:11]=1)=[O:9])[CH:4]([CH3:6])[CH3:5].[H-].[Na+]>O1CCCC1>[CH:4]([CH:3]1[CH2:2][O:9][C:8]([C:10]2[C:14]3[CH:15]=[C:16]([N:19]4[C:24](=[O:25])[CH:23]=[C:22]([C:26]([F:28])([F:29])[F:27])[N:21]([CH3:30])[C:20]4=[O:31])[CH:17]=[CH:18][C:13]=3[S:12][N:11]=2)=[N:7]1)([CH3:5])[CH3:6]

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 20634281N-[1-(Chloromethyl)-2-methylpropyl]-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-1,2-benzisothiazole-3-carboxamide

Product 1

HCID 206342283-[3-(4-Isopropyl-2-oxazolin-2-yl)-1,2-benzisothiazol-5-yl]-1-methyl-6-(trifluoromethyl)uracil

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of N-[1-(chloromethyl)-2-methylpropyl]-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-1,2-benzisothiazole-3-carboxamide(1.25 g, 2.63 mmol) in anhydrous tetrahydrofuran is added sodium hydride (60% oil dispersion, 0.116 g, 2.90 mmol). The resultant mixture is stirred 1.5 hour at room temperature, quenched with saturated ammonium chloride, diluted with diethyl ether, washed with saturated ammonium chloride and brine, and dried over anhydrous magnesium sulfate. Concentration in vacuo affords a yellow syrup, which is combined with material from a previous run and chromatographed on silica gel to afford the title compound as a white crystalline solid (mp 100-105° C.) which is identified by NMR spectral analysis.

Workup

  1. customquenched with saturated ammonium chloride
  2. additiondiluted with diethyl ether
  3. washwashed with saturated ammonium chloride and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationConcentration in vacuo
  6. customaffords a yellow syrup, which
  7. customchromatographed on silica gel

Sources & evidence

ORD record
ord-1c518f2cfec5428f8f711d532752799c
Source dataset
uspto-grants-2004_03
Patent number
US06706663B2

Reaction notes

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