1,3-Dichloro-2-propanol → 1,3-Bis(2-(dimethylamino)ethylthio)-2-propanol

HRID 581645Notes

Reaction equation

HRID 581645 reaction equation
Cl.[CH3:2][N:3]([CH3:7])[CH2:4][CH2:5][SH:6].[OH-].[Na+].Cl[CH2:11][CH:12]([OH:15])[CH2:13]Cl>C(O)C>[CH3:2][N:3]([CH3:7])[CH2:4][CH2:5][S:6][CH2:11][CH:12]([OH:15])[CH2:13][S:6][CH2:5][CH2:4][N:3]([CH3:7])[CH3:2]

Participants

5

Reactant 3

HCID 72891,3-Dichloro-2-propanolHCID 14798Sodium HydroxideHCID 25798Captamine Hydrochloride

Product 1

HCID 538484991,3-Bis(2-(dimethylamino)ethylthio)-2-propanolYield 85.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

2-(Dimethylamino)ethanethiol hydrochloride (10.78 g, 78 mmole) was added portion-wise to a solution of sodium hydroxide (6.2 g, 155 mmole) in ethanol (40 mL) at 0° C. under nitrogen. A further portion of ethanol (20 mL) was added and the mixture stirred at this temperature for 10 minutes. 1,3-Dichloro-2-propanol (5.29 g, 41 mmole) was added dropwise. On completion of the addition, the reaction mixture was allowed to warm to room temperature and stirred for a further 2 hours. The precipitated solid was filtered off and the washed with ethanol. The filtrate was evaporated. The resulting oil was taken up into acetone, filtered and evaporated to give the desired product (8.90 g, 68%) as a pale yellow oil.

Workup

  1. additionOn completion of the addition
  2. stirringstirred for a further 2 hours
  3. filtrationThe precipitated solid was filtered off
  4. washthe washed with ethanol
  5. customThe filtrate was evaporated
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-7f7856a28c464f0c9a0eed16e605b3c2
Source dataset
uspto-grants-1999_07
Patent number
US05922527

Reaction notes

Loading…