Dimethyl Sulfoxide → HCID 20554019, compound

HRID 1105997Notes

Reaction equation

HRID 1105997 reaction equation
[C:1](=[O:4])([O-])[O-].[K+].[K+].[Cl:7][C:8]1[CH:25]=[C:24]([C:26]([F:29])([F:28])[F:27])[CH:23]=[CH:22][C:9]=1[O:10][C:11]1[CH:12]=[C:13]([C:18]([Cl:21])=[CH:19][CH:20]=1)[O:14][CH:15](Cl)[CH3:16].[C:30](OC)(=O)[CH2:31][SH:32].CS(C)=O>CCOCC>[Cl:7][C:8]1[CH:25]=[C:24]([C:26]([F:29])([F:27])[F:28])[CH:23]=[CH:22][C:9]=1[O:10][C:11]1[CH:12]=[C:13]([C:18]([Cl:21])=[CH:19][CH:20]=1)[O:14][CH2:15][CH2:16][CH2:30][C:31]([O:4][CH3:1])=[S:32]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 11430Potassium CarbonateHCID 16907Methyl ThioglycolateHCID 86738210HCID 86738210, compound

Product 1

HCID 20554019HCID 20554019, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

20.7 g of potassium carbonate, 19.2 g (0.05 mole) of 3-(2'-chloro-4'-trifluoromethylphenoxy)-6-chlorophenoxy-chloroethane and 5.3 g (0.05 mole) of methyl thioglycolate are added at room temperature to 80 ml of dimethyl sulfoxide. In the course of the exothermic reaction, the temperature rises to about 42° C. The reaction mixture is then stirred overnight at room temperature. On the next day, the batch is diluted with 300 ml of ether and the ethereal solution is washed with two 400 ml portions of 20% K2CO3 solution. The organic phase is dried over magnesium sulfate and concentrated, affording 17.8 g of a light yellow oil with a refractive index of nD21 1.5487. The following compounds were obtained in analogous manner:

Workup

  1. customIn the course of the exothermic reaction
  2. customrises to about 42° C
  3. washthe ethereal solution is washed with two 400 ml portions of 20% K2CO3 solution
  4. dry with materialThe organic phase is dried over magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-c514977cb196488f9ceced97ff9ef8bf
Source dataset
uspto-grants-1982_01
Patent number
US04311514

Reaction notes

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