Dimethyl Sulfide → HCID 17777150, compound

HRID 583070Notes

Reaction equation

HRID 583070 reaction equation
[O:1]=[S:2]1(=[O:23])[N:7]([CH:8]([CH3:10])[CH3:9])[CH2:6][C:5]2[CH:11]=[CH:12][CH:13]=[C:14]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[C:4]=2[N:3]1[CH2:20][CH:21]=C.[O:24]=[O+][O-].CSC>ClCCl>[O:1]=[S:2]1(=[O:23])[N:7]([CH:8]([CH3:9])[CH3:10])[CH2:6][C:5]2[CH:11]=[CH:12][CH:13]=[C:14]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[C:4]=2[N:3]1[CH2:20][CH:21]=[O:24]

Participants

5

Reactant 3

HCID 1068Dimethyl SulfideHCID 24823OzoneHCID 17777154HCID 17777154, compound

Product 1

HCID 17777150HCID 17777150, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-75 °C

Procedure

Ethyl 3,4-dihydro-2,2-dioxo-3-(1-methylethyl)-1-(prop-2-en-1-yl)-1H-2,1,3-benzothiadiazine-8-carboxylate (1.1 g)(prepared from ethyl 3,4-dihydro-2,2-dioxo-3-(1-methylethyl)-1H-2,1,3-benzothiadiazine-8-carboxylate and (prop-2-en-1-yl) bromide) was dissolved in dichloromethane (80 ml) and cooled to -75° C. Ozone was passed through the solution until the solution became blue. At which time, dimethyl sulfide (5 ml) was added and the solution allowed to come to room temperature over 1 hour. The solution was washed with water to remove the DMSO present, dried over anhydrous magnesium sulfate, filtered and evaporated in vacuo to give a solid, ethyl 3,4-dihydro-2,2-dioxo-3-(1-methylethyl)-1-(2-oxoethyl)-1H-2,1,3-benzothiadiazine-8-carboxylate. This was dissolved in dichloroethane (50 ml) containing glacial acetic acid(5 drops) together with 4-(6-fluoroindol-3-yl)-1,2,5,6-tetrahydropyridine (0.8 g, 1.1 equiv.). Sodium triacetoxy borohydride (0.8 g, 1.1 equiv.) was added and the solution stirred overnight at room temperature. After washing with 2N sodium hydroxide (30 ml) and brine, the solution was dried, filtered and evacuated in vacuo to yield an off-white solid. Column chromatography eluting with ethyl acetate/hexane to ethyl acetate gave the required product, ethyl 3,4-dihydro-2,2-dioxo-1-{2-[4-(6-fluoroindol-3-yl)-1,2,5,6-tetrahydro-1-pyridyl]-1-ethyl}-3-(1-methylethyl)-1H-2,1,3-benzothiadiazine-8-carboxylate, m.p. 95-97° C.

Workup

  1. washThe solution was washed with water
  2. customto remove the DMSO present
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-7f08e79701cd4d0b9761993ae6ab6ee2
Source dataset
uspto-grants-1999_07
Patent number
US05929072

Reaction notes

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