Water → HCID 135840835, compound

HRID 1274613Notes

Reaction equation

HRID 1274613 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:12]2[CH:13]=[C:14]([N:17]3[C:22](=[O:23])[CH:21]=[C:20]([C:24]([F:27])([F:26])[F:25])[N:19]([CH3:28])[C:18]3=[O:29])[CH:15]=[CH:16][C:11]=2[S:10][N:9]=1.C(N(CC)CC)C.[S:37]([O:44]S(C(F)(F)F)(=O)=O)([C:40]([F:43])([F:42])[F:41])(=[O:39])=[O:38].O>C(Cl)Cl.C(OCC)C>[F:41][C:40]([S:37]([OH:44])(=[O:39])=[O:38])([F:43])[F:42].[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:12]2[CH:13]=[C:14]([N:17]3[C:22](=[O:23])[CH:21]=[C:20]([C:24]([F:27])([F:26])[F:25])[N:19]([CH3:28])[C:18]3=[O:29])[CH:15]=[CH:16][C:11]=2[S:10][N:9]=1

Participants

7

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 67749Trifluoromethanesulfonic anhydrideHCID 135840836HCID 135840836, compound

Product 1

HCID 135840835HCID 135840835, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent2×

Procedure

A mixture of 3-[3-(o-hydroxyphenyl)-1,2-benzisothiazol-5-yl]-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione (3.67 g, 8.75 mmol) and triethylamine (0.970 g, 9.63 mmol) in methylene chloride is cooled with an ice-water bath, treated with triflic anhydride (2.72 g, 9.63 mmol), stirred at room temperature overnight, and poured into water. The resultant aqueous mixture is extracted with methylene chloride. The organic extracts are combined, washed with brine, dried over anhydrous magnesium sulfate, and concentrated in vacuo to obtain an oil. Column chromatography of the oil using silica gel and a 3% diethyl ether in methylene chloride solution gives the title product as a white foam which is identified by NMR spectral analyses.

Workup

  1. temperatureis cooled with an ice-water bath
  2. extractionThe resultant aqueous mixture is extracted with methylene chloride
  3. washwashed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customto obtain an oil

Sources & evidence

ORD record
ord-eccaad2d6b254e37a142030e46d4063b
Source dataset
uspto-grants-2000_12
Patent number
US06156700

Reaction notes

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