Iodine → 3,3'-Disulfanediylbis(N,N-dimethylpropan-1-amine)

HRID 895039Notes

Reaction equation

HRID 895039 reaction equation
II.[CH3:3][N:4]([CH3:9])[CH2:5][CH2:6][CH2:7][SH:8].[OH-].[Na+]>CCOCC>[CH3:3][N:4]([CH3:9])[CH2:5][CH2:6][CH2:7][S:8][S:8][CH2:7][CH2:6][CH2:5][N:4]([CH3:9])[CH3:3]

Participants

5

Reactant 3

HCID 807Iodine2×HCID 14798Sodium HydroxideHCID 30169983-(DIMETHYLAMINO)-1-PROPANETHIOL

Product 1

HCID 2477763,3'-Disulfanediylbis(N,N-dimethylpropan-1-amine)Yield 68.1%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Iodine is added portionwise to a mixture of 4 g of 3-dimethylaminopropylmercaptan in 60 ml of ether and 30 ml of 2-N sodium hydroxide solution until the solution is no longer decolorised each time (ca 4.2 g of iodine). After stirring for 1 hour, the ether phase is dried over magnesium sulphate, concentrated and fractionally distilled at 95°-100° C./0.025 mmHg. 2.7 g (68%) of 3-dimethylaminopropyl disulphide are obtained in the form of a clear colourless liquid.

Workup

  1. dry with materialthe ether phase is dried over magnesium sulphate
  2. concentrationconcentrated
  3. distillationfractionally distilled at 95°-100° C./0.025 mmHg

Sources & evidence

ORD record
ord-8d4c3d502ae24f3c85d597ccf02b3086
Source dataset
uspto-grants-1981_08
Patent number
US04285984

Reaction notes

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