Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)- → 1-Benzylideneamino-3-propyltetrahydrocyclopenta[d]imidazol-2,5(1H,3H)-dione

HRID 1885897Notes

Reaction equation

HRID 1885897 reaction equation
O1[C:5]2([CH2:9][CH:8]([N:10]([C:19]([NH:21][CH2:22][CH2:23][CH3:24])=[O:20])[N:11]=[CH:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH:7]=[CH:6]2)[O:4]CC1.C12(CS(O)(=O)=O)C(C)(C)C(CC1)CC2=O>CC(C)=O>[CH:12](=[N:11][N:10]1[CH:8]2[CH2:9][C:5](=[O:4])[CH2:6][CH:7]2[N:21]([CH2:22][CH2:23][CH3:24])[C:19]1=[O:20])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 18462Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)-HCID 54263215Benzaldehyde 2-(1,4-dioxaspiro[4.4]non-6-en-8-yl)-4-propylsemicarbazone

Product 1

HCID 544413591-Benzylideneamino-3-propyltetrahydrocyclopenta[d]imidazol-2,5(1H,3H)-dioneYield 115.4%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

An acetone solution (150 ml) of the compound of step (d) (21 g) was stirred at 15° C. while camphorsulphonic acid (2.5 g) was added portionwise over 10 minutes. After 4 hours, the mixture was concentrated in vacuo, water (150 ml) and chloroform (100 ml) added and the organic phase separated. The latter was washed with dilute sodium bicarbonate (100 ml), separated and concentrated in vacuo to give the desired product as a brown oil (21.0 g).

Workup

  1. additionwas added portionwise over 10 minutes
  2. concentrationthe mixture was concentrated in vacuo, water (150 ml) and chloroform (100 ml)
  3. additionadded
  4. customthe organic phase separated
  5. washThe latter was washed with dilute sodium bicarbonate (100 ml)
  6. customseparated
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9f30f5af59f94829875563502685d01d
Source dataset
uspto-grants-1992_09
Patent number
US05147885

Reaction notes

Loading…