Dimethyl Sulfoxide → HCID 86608433, compound

HRID 1431963Notes

Reaction equation

HRID 1431963 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-aff8d128f25c48bca27bb93a79ab984c
Source dataset
uspto-grants-2009_11
Patent number
US07612061B2

Reaction notes

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