Methylamine → N-(4,4,6,6-tetramethyl-1,3-dithian-2-ylmethyl)methylamine

HRID 127142Notes

Reaction equation

HRID 127142 reaction equation
Cl[CH2:2][CH:3]1[S:8][C:7]([CH3:10])([CH3:9])[CH2:6][C:5]([CH3:12])([CH3:11])[S:4]1.[OH-].[Na+].[CH3:15][NH2:16]>>[CH3:11][C:5]1([CH3:12])[CH2:6][C:7]([CH3:10])([CH3:9])[S:8][CH:3]([CH2:2][NH:16][CH3:15])[S:4]1

Participants

4

Reactant 3

HCID 6329MethylamineHCID 14798Sodium HydroxideHCID 202861232-Chloromethyl-4,4,6,6-tetramethyl-1,3-dithiane

Product 1

HCID 53834633N-(4,4,6,6-tetramethyl-1,3-dithian-2-ylmethyl)methylamine

Conditions

Temperature
100 °C

Procedure

2-Chloromethyl-4,4,6,6-tetramethyl-1,3-dithiane (60 grams) and 40% aqueous methylamine (160 ml) are charged into a pressure vessel and heated, with agitation, at a temperature of about 100° C. for a period of about 16 hours under autogeneous pressure. At the end of this period, the reaction mixture is cooled to room temperature and 16 grams of sodium hydroxide are added. The resulting mixture is extracted with methylene chloride. The extract is dried, then stripped of solvent to yield the desired product N-(4,4,6,6-tetramethyl-1,3-dithian-2-ylmethyl)methylamine.

Workup

  1. temperatureAt the end of this period, the reaction mixture is cooled to room temperature
  2. extractionThe resulting mixture is extracted with methylene chloride
  3. customThe extract is dried

Sources & evidence

ORD record
ord-f8901deb3e4f4b5a849cab9c052adb11
Source dataset
uspto-grants-1981_03
Patent number
US04255182

Reaction notes

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