p-Toluenesulfonic acid monohydrate → HCID 10221407, compound

HRID 1250881Notes

Reaction equation

HRID 1250881 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:16])=[C:6]([NH:8][CH2:9][CH2:10][CH2:11][NH:12][CH:13]([CH3:15])[CH3:14])[CH:7]=1.O.C1(C)C=C[C:21]([S:24](O)(=O)=O)=CC=1>O1CCOCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:16])=[C:6]([N:8]2[CH2:9][CH2:10][CH2:11][N:12]([CH:13]([CH3:14])[CH3:15])[C:21]2=[S:24])[CH:7]=1

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 18324824HCID 18324824, compound

Product 1

HCID 10221407HCID 10221407, compoundYield 76.4%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a suspension of the diamine of Step C (6.47 g) in dioxane (100 mL) was added N,N′-thiocarbonyl-di-1,2,4-triazole (4.85 g) and the mixture was stirred at room temperature for 2 hours. Para-toluenesulfonic acid monohydrate (7.07 g) was added and the reaction mixture was heated at reflux under nitrogen until the reaction was complete by TLC (31 hours). Upon cooling the mixture was evaporated to dryness. The solid residue was redissolved in ethyl acetate, the solution was washed with water and brine, dried over magnesium sulfate and evaporated to dryness. The residue was dissolved in dichloromethane and absorbed onto a column of Merck-60 flash silica gel packed in hexane. Elution with a gradient of 20-25% ethyl acetate in hexane provided the title compound (5.81 g, 76.4%) as a white solid which was further triturated in hexane, m.p. 176-178° C.

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureat reflux under nitrogen until the reaction
  3. customwas complete by TLC (31 hours)
  4. temperatureUpon cooling the mixture
  5. customwas evaporated to dryness
  6. dissolutionThe solid residue was redissolved in ethyl acetate
  7. washthe solution was washed with water and brine
  8. dry with materialdried over magnesium sulfate
  9. customevaporated to dryness
  10. dissolutionThe residue was dissolved in dichloromethane
  11. customabsorbed onto a column of Merck-60 flash silica gel
  12. washElution with a gradient of 20-25% ethyl acetate in hexane

Sources & evidence

ORD record
ord-49d6474be16e462aa1e9890dc53d55a5
Source dataset
uspto-grants-2002_01
Patent number
US06340687B1

Reaction notes

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