p-Toluenesulfonic acid → HCID 176531325, compound

HRID 1278787Notes

Reaction equation

HRID 1278787 reaction equation
[CH:1](=O)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11].C(=O)(O)O.[NH2:17][NH:18][C:19]([NH2:21])=[NH:20].C1(C)C=CC(S(O)(=O)=O)=CC=1>O.C1(C)C=CC=CC=1>[CH:1](=[N:17][NH:18][C:19]([NH2:21])=[NH:20])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11]

Participants

6

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 8186UndecanalHCID 178513185HCID 178513185, compound

Product 1

HCID 176531325HCID 176531325, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 1140TolueneSolvent

Procedure

1 mol (170.3 g) of undecanal, 1.1 mol (150 g) of aminoguanidine hydrogen carbonate and 1 g of p-toluenesulphonic acid are mixed with 500 ml of toluene and refluxed with stirring. As soon as 2 mol of water have been separated using the water separator, the mixture is allowed to cool, concentrated by rotary evaporation and the dark red oil is taken up in 250 ml of petroleum ether 40/60°. The precipitate formed is filtered and washed again with petroleum ether. For recrystallisation the precipitate is dissolved in ethyl acetate and mixed with petroleum ether at boiling temperature (boiling range 40 to 60° C.) until beginning to turn cloudy. Fine crystals are obtained, m.p. 101° C. The structure and purity of the compound were confirmed by analytical and spectroscopic data.

Workup

  1. temperaturerefluxed
  2. temperatureto cool
  3. concentrationconcentrated by rotary evaporation
  4. custom60°
  5. customThe precipitate formed
  6. filtrationis filtered
  7. washwashed again with petroleum ether
  8. customFor recrystallisation the precipitate
  9. dissolutionis dissolved in ethyl acetate
  10. additionmixed with petroleum ether at boiling temperature (boiling range 40 to 60° C.)
  11. customFine crystals are obtained

Sources & evidence

ORD record
ord-027edf0e19144608a0680e0a4ad66544
Source dataset
uspto-grants-2002_09
Patent number
US06444706B2

Reaction notes

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