Dimethyl Sulfate → HCID 54497275, compound

HRID 358176Notes

Reaction equation

HRID 358176 reaction equation
[CH3:1][C:2]1([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[CH3:15])[O:6][CH:5]([CH3:7])[CH2:4][O:3]1.[CH2:16]([Li])CCC.CCCCCC.S(OC)(OC)(=O)=O>O1CCCC1.O>[CH3:1][C:2]1([N:8]([CH3:16])[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[CH3:15])[O:6][CH:5]([CH3:7])[CH2:4][O:3]1

Participants

7

Reactant 4

HCID 6497Dimethyl SulfateHCID 8058HexaneHCID 541461502,4-Dimethyl-2-(2-methylanilino)dioxolaneHCID 178418339Butyllithium

Product 1

HCID 54497275HCID 54497275, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-60 °C

Procedure

10.0 g (0.048 mole) of 2,4-dimethyl-2-(2-methylanilino)dioxolane was dissolved in about 150 ml of tetrahydrofuran and then cooled to -60° C. 30.15 ml of 1.6 molar n-butyl lithium in hexane (0.048 mole of n-butyl lithium) was added and the temperature of the mixture allowed to raise to 0° C. 4.6 ml (0.048 mole) of dimethyl sulfate was added dropwise at about 0°-10° C. The temperature of the mixture was allowed to raise to 25° C., then refluxed for 3 hours and then stirred overnight (about 15 hours) at room temperature. The mixture was then mixed with about 500 ml of water and extracted with ethyl ether. The ethyl ether extracts were combined, dried over magnesium sulfate and evaporated to dryness affording the title compound as an oil.

Workup

  1. temperatureto raise to 0° C
  2. temperatureto raise to 25° C.
  3. temperaturerefluxed for 3 hours
  4. extractionextracted with ethyl ether
  5. dry with materialdried over magnesium sulfate
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-4e9c8b1ba657490884709c303d65372b
Source dataset
uspto-grants-1984_08
Patent number
US04465502

Reaction notes

Loading…