2-Tridecanone → 2,3-Dihydroperimidine

HRID 1768898

Reaction equation

HRID 1768898 reaction equation
[NH2:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][C:10]=2[NH2:12])[CH:5]=[CH:4][CH:3]=1.[CH3:13]C(=O)CCCCCCCCCCC>O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C1(C)C=CC=CC=1>[NH:1]1[C:2]2=[C:11]3[C:6](=[CH:5][CH:4]=[CH:3]2)[CH:7]=[CH:8][CH:9]=[C:10]3[NH:12][CH2:13]1

Participants

5

Reactant 2

HCID 116222-TridecanoneHCID 680671,8-Diaminonaphthalene

Product 1

HCID 124409652,3-DihydroperimidineYield 174.3%

Reagents, catalysts & solvents 2

HCID 521998p-Toluenesulfonic acid monohydrateCatalystHCID 1140TolueneSolvent

Procedure

A stirred mixture of 26.05 g of 1,8-diaminonaphthalene, 32.66 g of 2-tridecanone, 55 mg of p-toluenesulfonic acid monohydrate, and 250 mL of toluene was heated to reflux under a nitrogen atmosphere using a Dean-Stark trap to remove the water evolved from the reaction for 5 hr. The mixture was then washed with saturated sodium bicarbonate solution, dried over anhydrous potassium carbonate, filtered, and the solvent removed under reduced pressure. The product was distilled to yield 48.86 g of dihydroperimidine intermediate, bp 192°-213° C. at 0.3 to 0.4 torr.

Workup

  1. temperaturewas heated
  2. temperatureto reflux under a nitrogen atmosphere
  3. customto remove the water
  4. customevolved from the reaction for 5 hr
  5. washThe mixture was then washed with saturated sodium bicarbonate solution
  6. dry with materialdried over anhydrous potassium carbonate
  7. filtrationfiltered
  8. customthe solvent removed under reduced pressure
  9. distillationThe product was distilled

Sources & evidence

ORD record
ord-e3e45563951a4d36ac60f60d1d047019
Source dataset
uspto-grants-1995_01
Patent number
US05380635

Linked notes

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