Dimethyl Sulfide → HCID 13366864, compound

HRID 1085804Notes

Reaction equation

HRID 1085804 reaction equation
S([O:6][CH3:7])(OC)(=O)=O.CSC.[N:11]1([CH:16]([C:18]([C:20]([CH3:30])([CH3:29])[CH2:21][C:22]2[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=2)=O)[CH3:17])[CH:15]=[N:14][CH:13]=[N:12]1.C[O-].[Na+]>C(#N)C>[Cl:28][C:25]1[CH:26]=[CH:27][C:22]([CH2:21][C:20]([C:18]2([CH:16]([N:11]3[CH:15]=[N:14][CH:13]=[N:12]3)[CH3:17])[CH2:7][O:6]2)([CH3:29])[CH3:30])=[CH:23][CH:24]=1

Participants

6

Reactant 4

HCID 1068Dimethyl SulfideHCID 6497Dimethyl SulfateHCID 10942334Sodium MethoxideHCID 20059007HCID 20059007, compound

Product 1

HCID 13366864HCID 13366864, compoundYield 98.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

A solution of 9.8 g (0.77 mole) of dimethyl sulphate and 5.3 g (0.085 mole) of dimethyl sulphide in 50 ml of acetonitrile is stirred at room temperature for 5 days. A solution of 13 g (0.044 mole) of 4-chlorophenyl-tert.butyl 1-(1,2,4-triazol-1-yl)-ethyl ketone in 20 ml of acetonitrile is then added dropwise at room temperature. At the same temperature, 4.8 g (0.088 mole) of sodium methylate are introduced and the mixture is subsequently stirred for 20 hours and then concentrated in vacuo. The residue is stirred overnight with a mixture of 35 ml of ethyl acetate and 25 ml of water. The organic phase is separated off, dried over sodium sulphate and concentrated in vacuo. 13.2 g (98.2% of theory) of 2-(4-chlorophenyl-tert.-butyl)-2-[1-(1,2,4-triazol-1-yl)-ethyl]oxirane of refractive index nD20 1.5431 are obtained.

Workup

  1. concentrationconcentrated in vacuo
  2. stirringThe residue is stirred overnight with a mixture of 35 ml of ethyl acetate and 25 ml of water
  3. customThe organic phase is separated off
  4. dry with materialdried over sodium sulphate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ebfc2a0721584bb1aa1901b40c1d3d31
Source dataset
uspto-grants-1991_04
Patent number
US05011850

Reaction notes

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