Dimethyl Sulfoxide → HCID 86760738, compound

HRID 2118062Notes

Reaction equation

HRID 2118062 reaction equation
[C:1](Cl)([C:3](Cl)=[O:4])=O.CS(C)=O.Cl[CH:12]([OH:17])[C:13]([CH3:16])([CH3:15])[CH3:14].CC1C=CC(S(O)(=O)=O)=[CH:23][CH:24]=1.[Cl:29]CCl>C(O)C.CCN(CC)CC>[Cl:29][CH2:14][C:13]([CH3:16])([CH3:15])[CH:12]([O:17][CH2:23][CH3:24])[O:4][CH2:3][CH3:1]

Participants

8

Reactant 5

HCID 679Dimethyl SulfoxideHCID 6101p-Toluenesulfonic acidHCID 6344Dichloromethane3×HCID 65578Oxalyl chlorideHCID 20401163HCID 20401163, compound

Product 1

HCID 86760738HCID 86760738, compoundYield 68%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8471TriethylamineSolvent

Procedure

A solution of 6.76 ml (77.5 mmol) de (COCl)2 in 220 ml of dry dichloromethane is cooled to −40° C. Then 153.8 ml (10.9 mmol) of dimethylsulfoxide are added slowly. 5 minutes later, a solution of 7.5 g of 1-chloro-2,2-dimethyl-propanol (formula (VIC): X=Cl) in 61 ml of dichloro-methane is added. The mixture is stirred for 15 minutes followed by the addition of 36 ml (264.3mmol) de Et3N. 30 ml of dichloromethane are added and the mixture is warmed to room temperature. The organic phase is washed with water (3×150 ml), dried over sodium sulfate, concentrated in vacuo (17° C./75 mbar). The oil obtained is solubilized in ethanol and the solution is heated under reflux with a catalytic amount of PTSA for 120 minutes, concentrated in vacuo (19° C./32 mbar). After distillation at 62-65° C. under 10 mbar, 8 g of compound (IVC) are obtained (yield: 68%).

Workup

  1. washThe organic phase is washed with water (3×150 ml)
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated in vacuo (17° C./75 mbar)
  4. customThe oil obtained
  5. temperaturethe solution is heated
  6. concentrationconcentrated in vacuo (19° C./32 mbar)
  7. distillationAfter distillation at 62-65° C. under 10 mbar, 8 g of compound (IVC)
  8. customare obtained (yield: 68%)

Sources & evidence

ORD record
ord-1a55e7952d784cceba004a7f8005388e
Source dataset
uspto-grants-2008_10
Patent number
US07442814B2

Reaction notes

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