Carbon Disulfide → Methyl morpholine-4-carbodithioate

HRID 572716Notes

Reaction equation

HRID 572716 reaction equation
[NH:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[C:7](=[S:9])=[S:8].[OH-].[Na+].S(OC)(O[CH3:16])(=O)=O>O>[N:1]1([C:7]([S:9][CH3:16])=[S:8])[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 6348Carbon DisulfideHCID 6497Dimethyl SulfateHCID 8083MorpholineHCID 14798Sodium Hydroxide

Product 1

HCID 5043631Methyl morpholine-4-carbodithioateYield 88.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirred solution of morpholine (201 mL, 2295 mmol) in water (2 L) was added carbon disulfide (0.138 L, 2295.67 mmol) under nitrogen. Sodium hydroxide (96 g, 2410 mmol in solution in 1 L of water) was then added dropwise. The resulting mixture was stirred at room temperature for 1 h, then cooled to 5° C. with an ice bath and dimethyl sulfate (217 mL, 2295 mmol) was added dropwise. The mixture was stirred 1 hr at room temperature, the obtained solid was collected by filtration, washed with water (2×1 L) and dried under vacuum over phosphorus pentoxide at 50° C. to give methyl morpholine-4-carbodithioate (360 g, 88%). NMR Spectrum: (CDCl3): 2.68 (s, 3H), 3.71-3.84 (m, 4H), 4.02 (bs, 2H), 4.30 (bs, 2H).

Workup

  1. temperaturecooled to 5° C. with an ice bath
  2. stirringThe mixture was stirred 1 hr at room temperature
  3. filtrationthe obtained solid was collected by filtration
  4. washwashed with water (2×1 L)
  5. dry with materialdried under vacuum over phosphorus pentoxide at 50° C.

Sources & evidence

ORD record
ord-25c8b47847214126bc41415a2d9faafb
Source dataset
uspto-grants-2015_05
Patent number
US09029374B2

Reaction notes

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