Carbon Disulfide → HCID 11020189, compound

HRID 1954476Notes

Reaction equation

HRID 1954476 reaction equation
[CH2:1]([C:3]1[CH:9]=[CH:8][C:6]([NH2:7])=[CH:5][CH:4]=1)[CH3:2].[C:10](=[S:12])=[S:11].[CH2:13](N(CC)CC)C.CCCCCC>C(OCC)C>[CH2:1]([C:3]1[CH:9]=[CH:8][C:6]([NH:7][C:10](=[S:12])[S:11][CH3:13])=[CH:5][CH:4]=1)[CH3:2]

Participants

6

Reactant 4

HCID 6348Carbon DisulfideHCID 8058HexaneHCID 8471TriethylamineHCID 115044-Ethylaniline

Product 1

HCID 11020189HCID 11020189, compoundYield 69.8%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of 4-ethylaniline (7.8 g) in diethyl ether (40 ml) were added carbon disulfide (6 g) and triethylamine (13 g). After stirring at room temperature for 2 hours, the precipitated crystals were collected by filtration and dried. The crystals (16 g) were dissolved in methanol (100 ml) and methyl iodide (7.6 g) was added dropwise thereto. The mixture was stirred at room temperature for 2 hours, acidified (pH =about 2) with in HCl and extracted with ethyl acetate. The organic phase was washed with water, dried over anhydrous magnesium sulfate and concentrated under reduced pressure to give a solid. The solid was treated with hexane, triturated, filtered and dried to give the desired methyl 4-ethylphenyldithiocarbamate (9.5 g, yield: 67%), m.p. 78° C.

Workup

  1. filtrationthe precipitated crystals were collected by filtration
  2. customdried
  3. dissolutionThe crystals (16 g) were dissolved in methanol (100 ml)
  4. additionmethyl iodide (7.6 g) was added dropwise
  5. stirringThe mixture was stirred at room temperature for 2 hours
  6. extractionextracted with ethyl acetate
  7. washThe organic phase was washed with water
  8. dry with materialdried over anhydrous magnesium sulfate
  9. concentrationconcentrated under reduced pressure
  10. customto give a solid
  11. customtriturated
  12. filtrationfiltered
  13. customdried

Sources & evidence

ORD record
ord-125b19df9f1d43aaa9bebd49ce51a070
Source dataset
uspto-grants-2000_09
Patent number
US06121476

Reaction notes

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