Sodium Carbonate → Methyl N-cyano-2-methylmorpholine-4-carbimidothioate

HRID 1958015Notes

Reaction equation

HRID 1958015 reaction equation
Cl.[CH3:2][CH:3]1[O:8][CH2:7][CH2:6][NH:5][CH2:4]1.[C:9]([N:11]=[C:12](SC)[S:13][CH3:14])#[N:10].C(=O)([O-])[O-].[Na+].[Na+]>C(O)C>[C:9]([N:11]=[C:12]([N:5]1[CH2:6][CH2:7][O:8][CH:3]([CH3:2])[CH2:4]1)[S:13][CH3:14])#[N:10]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 66289Dimethyl N-cyanodithioiminocarbonateHCID 226055572-Methylmorpholine--hydrogen chloride (1/1)

Product 1

HCID 80489835Methyl N-cyano-2-methylmorpholine-4-carbimidothioateYield 63.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2-methylmorpholine hydrochloride (1.0 g, 9.9 mmol), dimethyl cyanocarbonimidodithioate (1.45 g, 9.9 mmol) and sodium carbonate (0.2 g, 1.9 mmol) in ethanol (50 mL) was stirred at ambient temperature overnight. The reaction mixture was concentrated and purified through silica gel chromatography to give the desired product (1.25 g, 63%). LC-MS: 200 (MH+).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. custompurified through silica gel chromatography

Sources & evidence

ORD record
ord-59e310a4c4df43d89511b21394ac8827
Source dataset
uspto-grants-2013_04
Patent number
US08410095B2

Reaction notes

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