Carbon Disulfide → HCID 86761183, compound

HRID 1717433Notes

Reaction equation

HRID 1717433 reaction equation
[CH3:1][O:2][C:3]1[N:8]=[C:7]([NH:9][CH3:10])[CH:6]=[CH:5][CH:4]=1.[H-].[Na+:12].[C:13](=[S:15])=[S:14].CCCCCC>C1COCC1>[C:13](=[S:15])([S-:14])[NH2:8].[CH3:1][O:2][C:3]1[N:8]=[C:7]([NH:9][CH3:10])[CH:6]=[CH:5][CH:4]=1.[Na+:12]

Participants

6

Reactant 4

HCID 6348Carbon DisulfideHCID 8058HexaneHCID 24758Sodium hydrideHCID 70191686-methoxy-N-methylpyridin-2-amine

Product 1

HCID 86761183HCID 86761183, compoundYield 186.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

6-methoxy-2-methylaminopyridine (25.6 g, 0.185 mol) was dissolved in 120 ml of dehydrated THF, and 60% sodium hydride (7.4 g, 0.185 mol) was added. This was then refluxed for 1 hour, and upon becoming transparent, allowed to cool to room temperature. Carbon disulfide (14.1 g, 0.185 mol) was added dropwise into this solution, which was then stirred for two hours at room temperature. 300 ml of hexane were added and stirring continued until crystals precipitated out. The precipitated crystals were filtered out, then washed with 200 ml of hexane, and dried overnight in a dessicator to obtain 43.6 g (yield 99.7%) of the titled compound in the form of a pale yellow powder.

Workup

  1. temperatureThis was then refluxed for 1 hour
  2. stirringstirring
  3. customprecipitated out
  4. filtrationThe precipitated crystals were filtered out
  5. washwashed with 200 ml of hexane
  6. customdried overnight in a dessicator

Sources & evidence

ORD record
ord-e801af876e434e9baef260019b2c8296
Source dataset
uspto-grants-2010_09
Patent number
US07803947B2

Reaction notes

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