Dimethyl Sulfoxide → HCID 86608433, compound

HRID 2375257Notes

Reaction equation

HRID 2375257 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[OH:11][C@H:12]1[C@H:18]([N:19]2[CH2:24][CH2:23][N:22]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:21][CH2:20]2)[C:17]2[CH:32]=[CH:33][CH:34]=[CH:35][C:16]=2[O:15][CH2:14][CH2:13]1.C(N(CC)CC)C>ClCCl>[O:11]=[C:12]1[CH:18]([N:19]2[CH2:24][CH2:23][N:22]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:21][CH2:20]2)[C:17]2[CH:32]=[CH:33][CH:34]=[CH:35][C:16]=2[O:15][CH2:14][CH2:13]1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 86608434HCID 86608434, compound

Product 1

HCID 86608433HCID 86608433, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

At −78° C., 0.88 ml of oxalyl chloride (10 mmol) is poured into 25 ml of dichloromethane and then, at the same temperature, there are slowly added 1.02 ml of dimethyl sulphoxide (14.3 mmol). Stirring is carried out for 10 minutes at −78° C. 2.5 g (7.17 mmol) of the compound obtained in Step B of Example 8, dissolved in 15 ml of dichloromethane, are poured into the reaction mixture. Stirring is carried out for 15 minutes at −78° C. and there are then added, over 20 minutes, 5 ml (35.9 mmol) of triethylamine. The mixture is then allowed to return to 0° C. and the reaction mixture is then poured into 100 ml of ice-cold water. Extraction with dichloromethane, drying, filtration and evaporation to dryness are carried out to yield the expected product in the form of an oil.

Workup

  1. additionare poured into the reaction mixture
  2. stirringStirring
  3. waitis carried out for 15 minutes at −78° C.
  4. additionthere are then added, over 20 minutes
  5. customto return to 0° C.
  6. extractionExtraction with dichloromethane
  7. customdrying
  8. filtrationfiltration and evaporation to dryness

Sources & evidence

ORD record
ord-e085420a09714d9e8d4da3d370982d86
Source dataset
uspto-grants-2008_12
Patent number
US07465733B2

Reaction notes

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