Water → 1-Methyl-3-[3-(4-methyl-1,3-dioxolan-2-yl)-1,2-benzisothiazol-5-yl]-6-(trifluoromethyl)uracil

HRID 49006Notes

Reaction equation

HRID 49006 reaction equation
[CH3:1][N:2]1[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][C:5](=[O:12])[N:4]([C:13]2[CH:14]=[CH:15][C:16]3[S:20][N:19]=[C:18]([CH:21]=[O:22])[C:17]=3[CH:23]=2)[C:3]1=[O:24].[CH2:25](O)[CH:26]([OH:28])[CH3:27].C1(C)C=CC=CC=1.O>C(OCC)C.C1(C)C=CC(S(O)(=O)=O)=CC=1>[CH3:1][N:2]1[C:7]([C:8]([F:9])([F:10])[F:11])=[CH:6][C:5](=[O:12])[N:4]([C:13]2[CH:14]=[CH:15][C:16]3[S:20][N:19]=[C:18]([CH:21]4[O:28][CH:26]([CH3:27])[CH2:25][O:22]4)[C:17]=3[CH:23]=2)[C:3]1=[O:24]

Participants

7

Reactant 4

HCID 962WaterHCID 1030Propylene GlycolHCID 1140TolueneHCID 178523685-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-1, 2-benzisothiazole-3-carboxaldehyde

Product 1

HCID 206341811-Methyl-3-[3-(4-methyl-1,3-dioxolan-2-yl)-1,2-benzisothiazol-5-yl]-6-(trifluoromethyl)uracilYield 87.6%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 3283Diethyl EtherSolvent

Procedure

A mixture of 5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-1,2-benzisothiazole-3-carboxaldehyde (0.500 g, 1.41 mmol), 1,2-propanediol (0.130 ml, 1.83 mmol), p-toluenesulfonic acid (0.0100 g, 0.0100 g, 0.071 mmol) and toluene is stirred at reflux with azeotropic removal of water overnight, cooled to room temperature, diluted with diethyl ether, washed twice with water and once with brine and dried over anhydrous magnesium sulfate. Concentration in vacuo affords a yellow oil, which is chromatographed on silica gel to afford the title compound as a yellow solid (0.510 g, 87.6%, mp 81-83° C.) which is identified by NMR spectral analysis.

Workup

  1. washwashed twice with water and once with brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. concentrationConcentration in vacuo
  4. customaffords a yellow oil, which
  5. customis chromatographed on silica gel

Sources & evidence

ORD record
ord-a6c9a94d57604c4a80d996cf7541ff41
Source dataset
uspto-grants-2004_03
Patent number
US06706663B2

Reaction notes

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