HCID 20253472, compound → N-Methyl-2-{[2-(trimethylsilyl)ethyl]sulfanyl}ethan-1-amine

HRID 638156Notes

Reaction equation

HRID 638156 reaction equation
[CH:1]([NH:3][CH2:4][CH2:5][S:6][CH2:7][CH2:8][Si:9]([CH3:12])([CH3:11])[CH3:10])=O.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C(OCC)C>[CH3:1][NH:3][CH2:4][CH2:5][S:6][CH2:7][CH2:8][Si:9]([CH3:10])([CH3:12])[CH3:11]

Participants

4

Reactant 2

HCID 20253472HCID 20253472, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 15590151N-Methyl-2-{[2-(trimethylsilyl)ethyl]sulfanyl}ethan-1-amine

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A solution of 400 mg (2.00 mmol) of N-formyl-2-[[2-(trimethylsilyl)ethyl]thio]ethyl amine in 5 ml of absolute diethyl ether is added under argon at 0° C. to a stirred slurry of 152 mg (4.00 mmol) of lithium aluminum hydride in 5 ml of the same solvent. After 1 hr at 20° C., the stirred reaction mixture is quenched by addition of 0.6 ml of water and 0.15 ml of 15% sodium hydroxide solution, the resulting precipitate is filtered off, washed with diethyl ether. The combined organic layers is evaporated in vacuo, and the residue is distilled to N-methyl-2-[[2-(trimethylsilyl)ethyl]thio]ethyl amine (350 mg, 93.5%).

Workup

  1. customthe stirred reaction mixture
  2. customis quenched by addition of 0.6 ml of water and 0.15 ml of 15% sodium hydroxide solution
  3. filtrationthe resulting precipitate is filtered off
  4. washwashed with diethyl ether
  5. customThe combined organic layers is evaporated in vacuo
  6. distillationthe residue is distilled to N-methyl-2-[[2-(trimethylsilyl)ethyl]thio]ethyl amine (350 mg, 93.5%)

Sources & evidence

ORD record
ord-5331c310224e4663979cefc75c2f0228
Source dataset
uspto-grants-1985_12
Patent number
US04560679

Reaction notes

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