Hydrochloric Acid → HCID 19024927, compound

HRID 1033829Notes

Reaction equation

HRID 1033829 reaction equation
[CH3:1][O:2][CH2:3][C:4]([CH2:9][O:10][CH3:11])([SH:8])[CH2:5][NH:6][CH3:7].[OH-].[Na+].[CH2:14](Cl)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.Cl.C(=O)(O)[O-].[Na+]>CCOCC>[CH2:14]([S:8][C:4]([CH2:3][O:2][CH3:1])([CH2:9][O:10][CH3:11])[CH2:5][NH:6][CH3:7])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 7503Benzyl ChlorideHCID 14798Sodium HydroxideHCID 516892Sodium BicarbonateHCID 19024937HCID 19024937, compound

Product 1

HCID 19024927HCID 19024927, compoundYield 38.8%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

1,1-Bis(methoxymethyl)-2-(methylamino)ethanethiol (6 g) was stirred with aqueous sodium hydroxide (60 cm3, 2M) for a short time and then benzyl chloride (4.3 g) was added. This mixture was stirred at room temperature for 3 h and then made slightly acidic (~pH 4) by the addition of dilute hydrochloric acid. The mixture was extracted with chloroform, and the chloroform then removed under reduced pressure to give a viscous oil which gave a solid on trituration with ether. The free amine was liberated from the hydrochloride salt by the addition of saturated aqueous sodium bicarbonate and then extracted into chloroform. The chloroform extracts were dried (Na2SO4) and the solvent removed under reduced pressure to give the amine (3.5 g) as a brown oil.

Workup

  1. extractionThe mixture was extracted with chloroform
  2. customthe chloroform then removed under reduced pressure
  3. customto give a viscous oil which
  4. extractionextracted into chloroform
  5. dry with materialThe chloroform extracts were dried (Na2SO4)
  6. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-1dae06b0086245aea3c8497c8ff3495f
Source dataset
uspto-grants-1994_05
Patent number
US05312904

Reaction notes

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