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

HRID 839014Notes

Reaction equation

HRID 839014 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 2 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 2 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-41fa4d4c5c6744518c05127bba3c8ed5
Source dataset
uspto-grants-1978_06
Patent number
US04093723

Reaction notes

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