HCID 54212570, compound → HCID 23289830, compound

HRID 366405Notes

Reaction equation

HRID 366405 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]2[CH2:14][CH2:13][CH2:12][C:11]=2[C:15]#[N:16])[CH:5]=[C:6]([F:8])[CH:7]=1>[Ti](Cl)(Cl)(Cl)Cl.[OH-].[Na+]>[NH2:16][C:15]1[C:3]2[C:2]([F:1])=[CH:7][C:6]([F:8])=[CH:5][C:4]=2[N:9]=[C:10]2[CH2:14][CH2:13][CH2:12][C:11]=12

Participants

4

Reactant 1

HCID 54212570HCID 54212570, compound

Product 1

HCID 23289830HCID 23289830, compound

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 14798Sodium HydroxideSolvent

Conditions

Temperature
140 °C

Procedure

Under nitrogen, titanium tetrachloride (1.2 ml; 2.1 g; 11.0 mmol) was added to the above enamine (Example 38) (2.2 g, 10.0 mmol) and the stirred mixture was heated at 140° C. for 1 hour. After cooling, sodium hydroxide (10M, 20 ml) was added and the mixture heated under reflux for 1 hour. After being allowed to cool, this was filtered and the solids were washed with dichloromethane. Any organics in the filtrate were also extracted into dichloromethane, the extracts were combined, dried (Na2SO4), filtered and the solvent evaporated. Kugelrohr distillation (180° C., 0.02 mmHg) gave the product as a very pale yellow powder.

Workup

  1. temperatureAfter cooling
  2. temperaturethe mixture heated
  3. temperatureunder reflux for 1 hour
  4. temperatureto cool
  5. filtrationthis was filtered
  6. washthe solids were washed with dichloromethane
  7. extractionAny organics in the filtrate were also extracted into dichloromethane
  8. dry with materialdried (Na2SO4)
  9. filtrationfiltered
  10. customthe solvent evaporated
  11. distillationKugelrohr distillation (180° C., 0.02 mmHg)
  12. customgave the product as a very pale yellow powder

Sources & evidence

ORD record
ord-274e610b8e4541afbaf03d03c9b88141
Source dataset
uspto-grants-2000_10
Patent number
US06130228

Reaction notes

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