Dimethylamine → Tributyl[(methanesulfinyl)methyl]stannane

HRID 1288259Notes

Reaction equation

HRID 1288259 reaction equation
CN([Sn:4]([CH2:13][CH2:14][CH2:15][CH3:16])([CH2:9][CH2:10][CH2:11][CH3:12])[CH2:5][CH2:6][CH2:7][CH3:8])C.[CH3:17][S:18]([CH3:20])=[O:19].CNC>>[CH3:17][S:18]([CH2:20][Sn:4]([CH2:13][CH2:14][CH2:15][CH3:16])([CH2:9][CH2:10][CH2:11][CH3:12])[CH2:5][CH2:6][CH2:7][CH3:8])=[O:19]

Participants

4

Reactant 3

HCID 674DimethylamineHCID 679Dimethyl SulfoxideHCID 11034994Dimethylaminotri-n-butyltin

Product 1

HCID 21504810Tributyl[(methanesulfinyl)methyl]stannane

Procedure

Dimethylamino tributyltin (33.4 g.; 0.1 moles) and dimethylsulfoxide (100 g.; 1.28 moles) were stirred in a 250 ml reaction flask, under a positive pressure argon atmosphere, for 4.5 hours at 80° C. During the reaction, liberated dimethylamine gas exited from the reaction flask through an open port with the moving argon gas. The reaction stood overnight at ambient temperature. Excess dimethylsulfoxide was distilled at 75° C at 15 mm Hg. The reaction product was distilled through a semi-micro distillation apparatus at 138° C at 0.1 mm Hg. Yield of 25 g (68%) was identified as (methylsulfinylmethyl) tributyltin by 'H NMR and infrared spectra.

Workup

  1. customDuring the reaction
  2. distillationExcess dimethylsulfoxide was distilled at 75° C at 15 mm Hg
  3. distillationThe reaction product was distilled through a semi-micro distillation apparatus at 138° C at 0.1 mm Hg

Sources & evidence

ORD record
ord-7eaeb77a708b4ec8b9e880149d3fcbe4
Source dataset
uspto-grants-1976_10
Patent number
US03987191

Reaction notes

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