Methyl iodide → 10-{[(Methylsulfanyl)carbonothioyl]amino}decane-1-sulfonic acid

HRID 237153Notes

Reaction equation

HRID 237153 reaction equation
[OH-].[K+].[NH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][S:14]([OH:17])(=[O:16])=[O:15].[C:18](=[S:20])=[S:19].[CH3:21]I>C(O)C.O>[S:14]([CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][NH:3][C:18](=[S:20])[S:19][CH3:21])([OH:17])(=[O:15])=[O:16]

Participants

7

Reactant 4

HCID 6328Methyl iodideHCID 6348Carbon DisulfideHCID 14797Potassium HydroxideHCID 10354160HCID 10354160, compound

Product 1

HCID 2131509810-{[(Methylsulfanyl)carbonothioyl]amino}decane-1-sulfonic acid

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 962WaterSolvent

Procedure

A suspension of 56 g. (1.0 mol.) of potassium hydroxide and 118.7 g. (0.5 mol.) of 10-aminodecanesulfonic acid in 170 ml. of water is stirred for 30 minutes at 25°, then 40 g. (0.52 mol.) of carbon disulfide and 80 ml. of ethanol are added and the reaction mixture is stirred at 25° for 12 hours. The mixture is refluxed gently for two hours and cooled. Methyl iodide (71 g., 0.3 mol.) and 130 ml. of ethanol are added to the mixture and it is stirred at 25° for 12 hours. The mixture is evaporated to remove the ethanol and the solid residue is collected by filtration to give methyl 10-sulfodecyldithiocarbamate.

Workup

  1. additionA suspension of 56 g
  2. temperatureThe mixture is refluxed gently for two hours
  3. temperaturecooled
  4. stirringis stirred at 25° for 12 hours
  5. customThe mixture is evaporated
  6. customto remove the ethanol
  7. filtrationthe solid residue is collected by filtration

Sources & evidence

ORD record
ord-947ce2728d79483bb238649c5ab25b96
Source dataset
uspto-grants-1979_06
Patent number
US04159373

Reaction notes

Loading…