1,4-Dioxane → HCID 10198962, compound

HRID 1250894Notes

Reaction equation

HRID 1250894 reaction equation
[Cl:1][C:2]1[C:7]([NH:8][CH2:9][CH2:10][CH2:11][NH:12][CH3:13])=C(C)[CH:5]=[CH:4][CH:3]=1.O.C1(C)C=C[C:19]([S:22](O)(=O)=O)=CC=1.O1[CH2:32][CH2:31]OCC1>ClCCl>[Cl:1][C:2]1[C:7]([N:8]2[CH2:9][CH2:10][CH2:11][N:12]([CH3:13])[C:19]2=[S:22])=[C:31]([CH3:32])[CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 312751,4-DioxaneHCID 521998p-Toluenesulfonic acid monohydrate2×HCID 18324829HCID 18324829, compound

Product 1

HCID 10198962HCID 10198962, compoundYield 40.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of the diamine of Step A (4.16 g) in dioxane (110 mL) was added under nitrogen 1,1′-thiocarbonyl-di-1,2,4-triazole (7.12 g). After 30 minutes, para-toluenesulfonic acid monohydrate (15.1 g) was added and the reaction mixture was heated at reflux for 20 hours. More para-toluenesulfonic acid monohydrate (4.0 g) was added at this point, and after an additional 2.5 hours at reflux, the reaction was cooled and filtered. The filtrate was concentrated in vacuo to give an orange oil. The crude material was dissolved in dichloromethane and absorbed onto a column of Merck-60 flash silica gel. Elution with 20% ethyl acetate in hexane provided a white solid which was triturated with diethyl ether to give the title product (2.0 g, 40.3%) as a white solid, m.p. 164-165° C.

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureat reflux for 20 hours
  3. temperatureafter an additional 2.5 hours at reflux
  4. temperaturethe reaction was cooled
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated in vacuo
  7. customto give an orange oil
  8. customabsorbed onto a column of Merck-60 flash silica gel
  9. washElution with 20% ethyl acetate in hexane
  10. customprovided a white solid which
  11. customwas triturated with diethyl ether

Sources & evidence

ORD record
ord-cba2aa42b1064a07998e3b304a99d90f
Source dataset
uspto-grants-2002_01
Patent number
US06340687B1

Reaction notes

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