Hydrochloric Acid → HCID 86756093, compound

HRID 1274634Notes

Reaction equation

HRID 1274634 reaction equation
[C:1]([O:5][C:6](=[O:12])[NH:7][S:8]([CH3:11])(=[O:10])=[O:9])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].Br[CH2:16][C:17]1[C:21]2[CH:22]=[C:23]([N:26]3[C:31](=[O:32])[CH:30]=[C:29]([C:33]([F:36])([F:35])[F:34])[N:28]([CH3:37])[C:27]3=[O:38])[CH:24]=[CH:25][C:20]=2[S:19][N:18]=1.Cl>CS(C)=O.O1CCCC1>[CH3:37][N:28]1[C:29]([C:33]([F:34])([F:35])[F:36])=[CH:30][C:31](=[O:32])[N:26]([C:23]2[CH:24]=[CH:25][C:20]3[S:19][N:18]=[C:17]([CH2:16][N:7]([S:8]([CH3:11])(=[O:10])=[O:9])[C:6](=[O:12])[O:5][C:1]([CH3:4])([CH3:3])[CH3:2])[C:21]=3[CH:22]=2)[C:27]1=[O:38]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 10081367tert-Butyl methylsulfonylcarbamateHCID 22119928HCID 22119928, compound

Product 1

HCID 86756093HCID 86756093, compoundYield 78.7%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8028TetrahydrofuranSolvent

Procedure

tert-Butyl(methylsulfonyl)carbamate (1.52 g, 0.00780 mol) is added to a mixture of sodium hydride (60%, 0.312 g, 0.00780 mol) and tetrahydrofuran at 0° C. The mixture is allowed to come to room temperature. A solution of 3-[3-(bromomethyl)-1,2-benzisothiazol-5-yl]-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione (3.00 g, 0.00714 mol) in dimethyl sulfoxide is added dropwise. The resultant mixture is stirred overnight at room temperature, poured into dilute hydrochloric acid, and extracted with methylene chloride. The combined organic layers are washed with water, dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo. The resultant residue is chromatographed on silica gel with ether:methylene chloride to give the title compound as a white solid (3.00 g, 78.7%, mp 109-111° C.) which is identified by NMR spectral analysis.

Workup

  1. customto come to room temperature
  2. extractionextracted with methylene chloride
  3. washThe combined organic layers are washed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe resultant residue is chromatographed on silica gel with ether

Sources & evidence

ORD record
ord-b2a6c453629b4f90a6b4d03d0bc26bc0
Source dataset
uspto-grants-2000_12
Patent number
US06156700

Reaction notes

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