Dimethyl Sulfate → HCID 86647569, compound

HRID 1664079Notes

Reaction equation

HRID 1664079 reaction equation
[CH3:1][N:2]([CH3:16])[CH2:3][CH2:4][CH2:5][N:6]([C:8]1[CH:15]=[CH:14]C=[CH:12][C:9]=1C=O)[CH3:7].[S:17]([O:22]C)(O[CH3:21])(=[O:19])=[O:18].[C:24]([O:27][CH2:28][CH3:29])(=O)C>ClCCl>[CH3:24][S:17]([O-:22])(=[O:19])=[O:18].[CH:28]([C:29]1[CH:12]=[CH:9][C:8]([N:6]([CH3:7])[CH2:5][CH2:4][CH2:3][N+:2]([CH3:1])([CH3:16])[CH3:21])=[CH:15][CH:14]=1)=[O:27]

Participants

5

Reactant 3

HCID 6497Dimethyl SulfateHCID 8857Ethyl AcetateHCID 63695083HCID 63695083, compound

Product 1

HCID 86647569HCID 86647569, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

5 g of [[3-(dimethylamino)propyl](methyl)amino]benzaldehyde are diluted in 15 ml of dichloromethane. 2.36 ml of dimethyl sulphate diluted in 10 ml of dichloromethane are gradually added. The mixture is refluxed for 4 h and then cooled to ambient temperature and poured into 100 ml of ethyl acetate. The brown oil formed is separated by settling out, washed with 100 ml of EtOAc, taken up in 200 ml of methanol and concentrated under vacuum. It is subsequently dissolved in a saturated solution of sodium bicarbonate and of sodium chloride and extracted with butanol. The butanol phase is concentrated under vacuum and dried under vacuum in the presence of P2O5, and the product is then used for the subsequent step.

Workup

  1. additionare gradually added
  2. temperatureThe mixture is refluxed for 4 h
  3. customThe brown oil formed
  4. customis separated
  5. washwashed with 100 ml of EtOAc
  6. concentrationconcentrated under vacuum
  7. dissolutionIt is subsequently dissolved in a saturated solution of sodium bicarbonate and of sodium chloride
  8. extractionextracted with butanol
  9. concentrationThe butanol phase is concentrated under vacuum
  10. dry with materialdried under vacuum in the presence of P2O5

Sources & evidence

ORD record
ord-08d558de09714ef4b8b2e4fa0121159f
Source dataset
uspto-grants-2011_10
Patent number
US08038732B2

Reaction notes

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