Methyl iodide → 11-{[(Methylsulfanyl)carbonothioyl]amino}undecanoic acid

HRID 27134Notes

Reaction equation

HRID 27134 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][C:14]([OH:16])=[O:15].[C:17](=[S:19])=[S:18].[CH3:20]I>C(O)C.O>[C:14]([CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][NH:3][C:17](=[S:19])[S:18][CH3:20])([OH:16])=[O:15]

Participants

7

Reactant 4

HCID 6328Methyl iodideHCID 6348Carbon DisulfideHCID 14797Potassium HydroxideHCID 1708311-Aminoundecanoic acid

Product 1

HCID 2057407811-{[(Methylsulfanyl)carbonothioyl]amino}undecanoic acid

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 962WaterSolvent

Procedure

A suspension of 56 g. (1.0 mol.) of potassium hydroxide and 100 g. (0.5 mol.) of 11-aminoundecanoic acid in 170 ml. of water was stirred for 30 minutes at 25° then 40 g. (0.52 mol.) of carbon disulfide and 80 ml. of ethanol were added and the reaction mixture was stirred at 25° for 12 hours. The mixture was refluxed gently for two hours and cooled. Methyl iodide (71 g., 0.3 mol.) and 130 ml. of ethanol were added to the mixture and it was stirred at 25° for 12 hours. The mixture was evaporated to remove the ethanol and the solid residue was collected by filtration to give methyl 10-carboxydecyldithiocarbamate.

Workup

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

Sources & evidence

ORD record
ord-793b1a78e0fc48e9953bc342bff6b68e
Source dataset
uspto-grants-1980_09
Patent number
US04220644

Reaction notes

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