Dimethyl Sulfoxide → HCID 54122960, compound

HRID 2259712Notes

Reaction equation

HRID 2259712 reaction equation
CS(C)=O.[C:5](Cl)(=[O:9])[C:6](Cl)=O.[CH2:11]([N:13]([CH2:16][CH3:17])[CH2:14]C)[CH3:12]>ClCCl>[CH3:14][N:13]1[CH2:16][CH2:17][CH:12]([CH2:6][CH:5]=[O:9])[CH2:11]1

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chloride

Product 1

HCID 54122960HCID 54122960, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Dimethylsulphoxide (0.36 ml) was added dropwise to a solution of oxalyl chloride (0.33 ml) in dry dichloromethane (8 ml) at -72°, with stirring under nitrogen. The solution was stirred at -72° for 5 min then a solution of the compound of stage (i) (325 mg) in dry dichloromethane (5 ml) was added in a stream over 3 min. The solution was stirred at -72° for 15 min then triethylamine (1.75 ml) was added. The mixture was then warmed to room temperature over 1 h. The solvent and excess triethylamine were evaporated to give the crude title compound which was used immediately in the next step.

Workup

  1. stirringThe solution was stirred at -72° for 5 min
  2. stirringThe solution was stirred at -72° for 15 min
  3. customThe solvent and excess triethylamine were evaporated

Sources & evidence

ORD record
ord-e41ffc7a0f3d46d7ab0d043e615eea00
Source dataset
uspto-grants-1995_12
Patent number
US05475020

Reaction notes

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