Dimethyl Sulfoxide → HCID 19599952, compound

HRID 611397Notes

Reaction equation

HRID 611397 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[O:11]1[C:15]2[CH2:16][N:17]([S:20]([C:23]3[CH:30]=[CH:29][C:26]([CH2:27][OH:28])=[CH:25][CH:24]=3)(=[O:22])=[O:21])[CH2:18][CH2:19][C:14]=2[CH:13]=[CH:12]1.C(N(CC)CC)C>ClCCl.C(OCC)C>[O:11]1[C:15]2[CH2:16][N:17]([S:20]([C:23]3[CH:30]=[CH:29][C:26]([CH:27]=[O:28])=[CH:25][CH:24]=3)(=[O:22])=[O:21])[CH2:18][CH2:19][C:14]=2[CH:13]=[CH:12]1

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 53975890HCID 53975890, compound

Product 1

HCID 19599952HCID 19599952, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 1.07 g (8.44 mmol) of oxalyl chloride in 50 ml of dichloromethane, 1.20 ml (16.9 mmol) of dimethyl sulfoxide was added dropwise at -78° C., followed by stirring for 5 minutes. To this solution, a solution of 1.650 g of the above crude 4-(5,7-dihydro-4H-furo[2,3-c]pyridin-6-ylsulfonyl)benzyl alcohol in 10 ml of dichloromethane was added at -78° C., followed by stirring for 15 minutes. To this mixture, 4.70 ml (33.7 mmol) of triethylamine was added; the mixture was allowed to warm to room temperature. The reaction mixture was diluted with diethyl ether, washed with water and dried over anhydrous magnesium sulfate; the solvent was distilled off under reduced pressure. The resulting crude product was purified by silica gel column chromatography (dichloromethane) and crystallized from diethyl ether-hexane to yield the desired product.

Workup

  1. stirringby stirring for 15 minutes
  2. washwashed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationthe solvent was distilled off under reduced pressure
  5. customThe resulting crude product was purified by silica gel column chromatography (dichloromethane)
  6. customcrystallized from diethyl ether-hexane

Sources & evidence

ORD record
ord-0c50069ddc8f44bea9b54cb06a38999f
Source dataset
uspto-grants-1999_12
Patent number
US05998433

Reaction notes

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