Methanol → HCID 22119824, compound

HRID 1274640Notes

Reaction equation

HRID 1274640 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]([C:21]([OH:23])=[O:22])[C:17]=3[CH:24]=2)[C:3]1=[O:25].[CH3:26]O>S(=O)(=O)(O)O>[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]([C:21]([O:23][CH3:26])=[O:22])[C:17]=3[CH:24]=2)[C:3]1=[O:25]

Participants

4

Reactant 2

HCID 887MethanolHCID 111878605-[3,6-Dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-1,2-benzisothiazole-3-carboxylic acid

Product 1

HCID 22119824HCID 22119824, compoundYield 75.3%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidCatalyst

Procedure

To a solution of 5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-1,2-benzisothiazole-3-carboxylic acid (0.300 g, 0.000809 mol) in methanol is added sulfuric acid (98%, 5 drops) at room temperature. The resultant mixture is stirred overnight at room temperature and concentrated in vacuo. The residue is taken up in methylene chloride, washed with saturated sodium bicarbonate and brine, dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo. Column chromatography of the residue on silica gel with methylene chloride:ethyl acetate gives the title compound as a white solid (0.235 g, 75.3%, mp 153-156° C.).

Workup

  1. concentrationconcentrated in vacuo
  2. washwashed with saturated sodium bicarbonate and brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-fd454fdd5838470e894185925c87bf43
Source dataset
uspto-grants-2000_12
Patent number
US06156700

Reaction notes

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