Acetic Anhydride → HCID 18175004, compound

HRID 395581Notes

Reaction equation

HRID 395581 reaction equation
[N+:1]([C:4]1[CH:13]=[C:12]2[C:7]([CH2:8][CH2:9][CH2:10][C:11]2=[CH:14][C:15]#[N:16])=[CH:6][CH:5]=1)([O-])=O.[C:17]([O-:20])(=O)[CH3:18].[Na+].[C:22](OC(=O)C)(=[O:24])[CH3:23]>[Ni]>[C:22]([NH:16][CH2:15][CH2:14][CH:11]1[C:12]2[CH:13]=[C:4]([NH:1][C:17](=[O:20])[CH3:18])[CH:5]=[CH:6][C:7]=2[CH2:8][CH2:9][CH2:10]1)(=[O:24])[CH3:23]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 517045Sodium AcetateHCID 57116290HCID 57116290, compound

Product 1

HCID 18175004HCID 18175004, compound

Reagents, catalysts & solvents 1

HCID 935NickelCatalyst

Conditions

Temperature
55 °C

Procedure

9 mmol of the compound obtained in Step B are dissolved in acetic anhydride (100 ml) and then a small spatula of sodium acetate is added. The mixture is introduced into an autoclave, Raney nickel is added and autoclaving under a pressure of 40 bars is carried out for 6 hours, with stirring at 50-60° C. The mixture is filtered and is rinsed with alcohol at 95° C.; the solvent is then evaporated off. Hydrolysis is carried out using 100 ml of distilled water and extraction with 3 volumes of dichloromethane is carried out. The organic phase is washed with 2 volumes of water, dried over magnesium sulphate, filtered and evaporated. Rinsing with an ether/dichloromethane mixture and trituration in ether are carried out. The light-beige solid obtained is recrystallised.

Workup

  1. additionis added
  2. filtrationThe mixture is filtered
  3. washis rinsed with alcohol at 95° C.
  4. customthe solvent is then evaporated off
  5. customHydrolysis
  6. extraction100 ml of distilled water and extraction with 3 volumes of dichloromethane
  7. washThe organic phase is washed with 2 volumes of water
  8. dry with materialdried over magnesium sulphate
  9. filtrationfiltered
  10. customevaporated
  11. washRinsing with an ether/dichloromethane mixture and trituration in ether
  12. customThe light-beige solid obtained
  13. customis recrystallised

Sources & evidence

ORD record
ord-540d09772a4e4089b85ef8060df846c8
Source dataset
uspto-grants-2003_08
Patent number
US06605632B1

Reaction notes

Loading…