Dimethylamine → [(Benzenesulfinyl)methyl](tributyl)stannane

HRID 1288258Notes

Reaction equation

HRID 1288258 reaction equation
[CH3:1][S:2]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)=[O:3].CN([Sn:13]([CH2:22][CH2:23][CH2:24][CH3:25])([CH2:18][CH2:19][CH2:20][CH3:21])[CH2:14][CH2:15][CH2:16][CH3:17])C.CNC>>[C:4]1([S:2]([CH2:1][Sn:13]([CH2:18][CH2:19][CH2:20][CH3:21])([CH2:22][CH2:23][CH2:24][CH3:25])[CH2:14][CH2:15][CH2:16][CH3:17])=[O:3])[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

4

Reactant 3

HCID 674DimethylamineHCID 14516Methyl phenyl sulfoxideHCID 11034994Dimethylaminotri-n-butyltin

Product 1

HCID 15254406[(Benzenesulfinyl)methyl](tributyl)stannaneYield 65%

Procedure

Phenyl methyl sulfoxide (7.0 g.; 0.05 moles) and dimethylamino tributyltin (16.7 g.; 0.05 moles) were admixed in a 50 ml round bottom flask, under a positive pressure argon atmosphere, for 20 hours at 100° C. During the reaction, liberated dimethylamine gas exited from the reaction flask through an open port with the moving argon gas. The crude product was distilled through a semi-micro distillation apparatus. The main fraction (13 g; 65% yield) distilled at 160°-170° C at 0.05 mm Hg. The product was identified by 'H NMR and infra red spectra as (phenylsulfinylmethyl) tributyltin.

Workup

  1. customDuring the reaction
  2. distillationThe crude product was distilled through a semi-micro distillation apparatus
  3. distillationThe main fraction (13 g; 65% yield) distilled at 160°-170° C at 0.05 mm Hg

Sources & evidence

ORD record
ord-1366aa7cb8df405f95658468fe31e9e2
Source dataset
uspto-grants-1976_10
Patent number
US03987191

Reaction notes

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