N-Iodosuccinimide → HCID 70098814, compound

HRID 1274619Notes

Reaction equation

HRID 1274619 reaction equation
[I:1]N1C(=O)CCC1=O.[OH:9][C:10]1[C:15]([C:16]2[C:20]3[CH:21]=[C:22]([N:25]4[C:30](=[O:31])[CH:29]=[C:28]([C:32]([F:35])([F:34])[F:33])[N:27]([CH3:36])[C:26]4=[O:37])[CH:23]=[CH:24][C:19]=3[S:18][N:17]=2)=[CH:14][CH:13]=[CH:12][C:11]=1[CH3:38]>CC(C)=O>[OH:9][CH:10]1[C:15]([C:16]2[C:20]3[CH:21]=[C:22]([N:25]4[C:30](=[O:31])[CH:29]=[C:28]([C:32]([F:35])([F:34])[F:33])[N:27]([CH3:36])[C:26]4=[O:37])[CH:23]=[CH:24][C:19]=3[S:18][N:17]=2)([I:1])[CH:14]=[CH:13][CH:12]=[C:11]1[CH3:38]

Participants

4

Reactant 2

HCID 120273N-Iodosuccinimide2×HCID 135840834HCID 135840834, compound

Product 1

HCID 70098814HCID 70098814, compoundYield 50.3%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

A solution of N-iodosuccinimide (0.240 g, 0.00107 mol) in acetone is added dropwise to a solution of 3-[3-(2-hydroxy-m-tolyl)-1,2-benzisothiazol-5-yl]-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione (0.430 g, 0.000992 mol) in acetone and the resultant mixture is stirred overnight at room temperature. Additional N-iodosuccinimide (0.120 g, 0.000635 mol) is added and the mixture is stirred three hours at room temperature. The mixture is concentrated in vacuo to afford a red gum which is chromatographed on silica gel with ether:methylene chloride. The fractions containing the title compound are washed with 1M sodium thiosulfate and brine, dried over anyhdrous magnesium sulfate and concentrated in vacuo to afford the title compound as a yellow solid (0.280 g, 46.8%, mp 241-242° C.).

Workup

  1. concentrationThe mixture is concentrated in vacuo
  2. customto afford a red gum which
  3. customis chromatographed on silica gel with ether
  4. additionThe fractions containing the title compound
  5. washare washed with 1M sodium thiosulfate and brine
  6. dry with materialdried over anyhdrous magnesium sulfate
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-dd5440652a4b446793aaaa4186025b3b
Source dataset
uspto-grants-2000_12
Patent number
US06156700

Reaction notes

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