Carbon Disulfide → HCID 86224690, compound

HRID 1863937Notes

Reaction equation

HRID 1863937 reaction equation
Cl.Cl.[CH3:3][C:4]1[NH:8][N:7]=[C:6]([CH2:9][CH2:10][NH2:11])[N:5]=1.[OH-].[Na+].[C:14](=S)=[S:15].ClC(OCC)=O>O.C(O)C.C(O)(=O)C>[CH3:3][C:4]1[N:5]=[C:6]2[N:7]([C:14](=[S:15])[NH:11][CH2:10][CH2:9]2)[N:8]=1

Participants

8

Reactant 4

HCID 6348Carbon DisulfideHCID 10928Ethyl chloroformateHCID 14798Sodium HydroxideHCID 53407543HCID 53407543, compound

Product 1

HCID 86224690HCID 86224690, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A solution of 1.99 g (10 mmol) of 2-(5-methyl-1,2,4-triazol-3-yl)ethanamine dihydrochloride in a mixture of 13 mL of water and 7 mL (35 mmol) of 5N sodium hydroxide aqueous solution was stirred under nitrogen at room temperature as a solution of 5.4 mL of carbon disulfide in 30 mL of dry ethanol was added dropwise over about 30 minutes. After 5 h, the excess carbon disulfide was removed by rotary evaporation. The resulting solution was stirred under nitrogen at room temperature as 1.08 mL (1.23 g, 11 mmol) of ethyl chloroformate was added dropwise over about 10 minutes. Stirring at room temperature was continued overnight. The solution was partially concentrated to remove the ethanol, resulting in precipitation. The pH was made slightly acidic by addition of acetic acid. Then the solid was collected on a filter, washed with a small volume of water, and dried to give the title compound as a solid. LC-MS 169 (M+1).

Workup

  1. additionwas added dropwise over about 30 minutes
  2. customthe excess carbon disulfide was removed by rotary evaporation
  3. additionwas added dropwise over about 10 minutes
  4. waitwas continued overnight
  5. concentrationThe solution was partially concentrated
  6. customto remove the ethanol
  7. customresulting in precipitation
  8. customThen the solid was collected on a filter
  9. washwashed with a small volume of water
  10. customdried

Sources & evidence

ORD record
ord-91b1f9edb73148b19811eb9c9c5abf0b
Source dataset
uspto-grants-2009_12
Patent number
US07625888B2

Reaction notes

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