Dimethyl Sulfoxide → HCID 19760329, compound

HRID 1586969Notes

Reaction equation

HRID 1586969 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]3[NH:14][C:13]4[CH2:15][CH2:16][N:17]([C:19]5[CH:24]=[CH:23][C:22]([S:25]([CH3:28])(=[O:27])=[O:26])=[CH:21][CH:20]=5)[CH2:18][C:12]=4[C:7]=3[CH:8]=[N:9]2)=[CH:4][CH:3]=1.C([O-])([O-])=[O:30].[Cs+].[Cs+].C[N+]([O-])(C)C.CS(C)=O>O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[C:6]3[NH:14][C:13]([CH2:15][CH2:16][NH:17][C:19]4[CH:24]=[CH:23][C:22]([S:25]([CH3:28])(=[O:27])=[O:26])=[CH:21][CH:20]=4)=[C:12]([CH:18]=[O:30])[C:7]=3[CH:8]=[N:9][C:10]=2[CH:11]=1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 1145Trimethylamine oxideHCID 10796Cesium carbonateHCID 19102713HCID 19102713, compound

Product 1

HCID 19760329HCID 19760329, compoundYield 24.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 3.0 g (7.28 mmol) of the compound of step A, above, 4.74 g (14.6 mmol) of Cs2CO3, 1.62 g (14.6 mmol) of trimethylamine N-oxide and 24 ml of dimethyl sulfoxide is stirred at 120° C. for 4 days. The reaction mixture is cooled and diluted with 400 ml of water producing a brown precipitate which is collected by filtration. The crude product is dissolved in methanol, filtered and evaporated onto silica gel. The coated silica gel is then added to a column and eluted with 10% methanol in chloroform to yield 0.75 g (24%) of title compound as an off white solid.

Workup

  1. temperatureThe reaction mixture is cooled
  2. filtrationis collected by filtration
  3. dissolutionThe crude product is dissolved in methanol
  4. filtrationfiltered
  5. customevaporated onto silica gel
  6. additionThe coated silica gel is then added to a column
  7. washeluted with 10% methanol in chloroform

Sources & evidence

ORD record
ord-cd2518474dd64dd39d419fc3e622f029
Source dataset
uspto-grants-1993_06
Patent number
US05216162

Reaction notes

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