Acetic Acid → HCID 131722520, compound

HRID 324443Notes

Reaction equation

HRID 324443 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:8][CH2:9][C:10](=[O:19])[C:11](=[N:17]O)[C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:5]=[CH:6][CH:7]=1.O.[C:21](O)(=[O:23])[CH3:22]>C(OC(=O)C)(=O)C.[Zn]>[C:21]([NH:17][CH:11]([C:10](=[O:19])[CH2:9][CH2:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=1)[C:12]([O:14][CH2:15][CH3:16])=[O:13])(=[O:23])[CH3:22]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 962WaterHCID 178472912HCID 178472912, compound

Product 1

HCID 131722520HCID 131722520, compound

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 7918Acetic AnhydrideSolvent

Conditions

Temperature
40 °C

Procedure

To a stirred solution of the product from step (ii) in acetic acid (125 ml) and acetic anhydride (40 ml) was added zinc dust (45 g) portionwise at a rate to maintain the internal temperature <40° C. The mixture was stirred for 30 min and water (125 ml) was added at such a rate as to maintain the temperature at around 40° C. The mixture was stirred at room temperature for 2 hours and filtered. The mother liquor was extracted with dichloromethane and further washed with water. The organic layer was collected, dried (MgSO4) and solvent evaporated under reduced pressure to give the subtitle product.

Workup

  1. temperatureto maintain the internal temperature <40° C
  2. stirringThe mixture was stirred at room temperature for 2 hours
  3. filtrationfiltered
  4. extractionThe mother liquor was extracted with dichloromethane
  5. washfurther washed with water
  6. customThe organic layer was collected
  7. dry with materialdried (MgSO4) and solvent
  8. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-929d8174cd0040a28be49daa704866ea
Source dataset
uspto-grants-2001_04
Patent number
US06218376B1

Reaction notes

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