1-Chloroethyl chloroformate → 4-Methyl-4-phenyl-[1,4]azasilinane hydrochloride

HRID 40553Notes

Reaction equation

HRID 40553 reaction equation
C([N:8]1[CH2:13][CH2:12][Si:11]([CH3:20])([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:10][CH2:9]1)C1C=CC=CC=1.[Cl:21]C(OC(Cl)C)=O>ClCCl.C(OCC)(=O)C>[ClH:21].[CH3:20][Si:11]1([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]1

Participants

5

Reactant 2

HCID 5213051-Chloroethyl chloroformateHCID 669259441-Benzyl-4-methyl-4-phenyl-[1,4]azasilinane

Product 1

HCID 676071694-Methyl-4-phenyl-[1,4]azasilinane hydrochloride

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

3.6 g of 1-benzyl-4-methyl-4-phenyl-[1,4]azasilinane is put in 32 ml of anhydrous dichloromethane under nitrogen. At 0° C., 2.5 ml of 1-chloroethyl chloroformate is added dropwise to the reaction mixture. The reaction mixture is gradually brought back to room temperature and then stirred for 2 h under reflux. After complete conversion, the reaction mixture is concentrated under vacuum and dried, then the residue is dissolved in 50 ml of methanol at room temperature. The mixture is stirred under reflux for 2 h. After evaporation of the solvent under vacuum, the yellow solid obtained is then suspended in ethyl acetate. The suspension is refluxed for some minutes and then gradually cooled to room temperature. The crystals thus formed are filtered, washed with ethyl acetate and dried under vacuum. 2.13 g of 4-methyl-4-phenyl-[1,4]azasilinane hydrochloride is obtained in the form of white crystals.

Workup

  1. customis gradually brought back to room temperature
  2. temperatureunder reflux
  3. concentrationAfter complete conversion, the reaction mixture is concentrated under vacuum
  4. customdried
  5. dissolutionthe residue is dissolved in 50 ml of methanol at room temperature
  6. stirringThe mixture is stirred
  7. temperatureunder reflux for 2 h
  8. customAfter evaporation of the solvent under vacuum
  9. customthe yellow solid obtained
  10. temperatureThe suspension is refluxed for some minutes
  11. customThe crystals thus formed
  12. filtrationare filtered
  13. washwashed with ethyl acetate
  14. customdried under vacuum

Sources & evidence

ORD record
ord-cd0063e61c1146d68284f6cb64a667d0
Source dataset
uspto-grants-2013_09
Patent number
US08530473B2

Reaction notes

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