Acetic Anhydride → HCID 15482068, compound

HRID 380243Notes

Reaction equation

HRID 380243 reaction equation
[Cl:1][C:2]1[CH:22]=[CH:21][C:5]([O:6][C:7]2[C:8]3[CH:17]=[C:16]4[O:18][CH2:19][O:20][C:15]4=[CH:14][C:9]=3[S:10][C:11]=2[CH:12]=O)=[CH:4][CH:3]=1.[N:23]1[CH:28]=[CH:27][C:26]([CH2:29][C:30]([O:32][CH2:33][CH3:34])=[O:31])=[CH:25][CH:24]=1.C(OC(=O)C)(=O)C.C([O-])(O)=O.[Na+]>>[Cl:1][C:2]1[CH:22]=[CH:21][C:5]([O:6][C:7]2[C:8]3[CH:17]=[C:16]4[O:18][CH2:19][O:20][C:15]4=[CH:14][C:9]=3[S:10][C:11]=2/[CH:12]=[C:29](\[C:26]2[CH:27]=[CH:28][N:23]=[CH:24][CH:25]=2)/[C:30]([O:32][CH2:33][CH3:34])=[O:31])=[CH:4][CH:3]=1

Participants

5

Reactant 4

HCID 7918Acetic AnhydrideHCID 516892Sodium BicarbonateHCID 736321Ethyl pyridine-4-acetateHCID 15482077HCID 15482077, compound

Product 1

HCID 15482068HCID 15482068, compound

Conditions

Temperature
100 °C

Procedure

A solution containing 85 mmol of the product obtained in Step E, 127 mmol of ethyl 4-pyridylacetate and 75 ml of acetic anhydride is heated at 100° C. for 18 hours. After returning to ambient temperature, the reaction mixture is hydrolysed by saturated NaHCO3 solution and extracted with ethyl acetate. The organic phases are then washed with water and then with NaCl solution, dried over calcium sulphate, filtered and concentrated under reduced pressure. Chromatography over silica gel (dichloromethane/ethanol : 98/2) allows the expected product to be isolated.

Workup

  1. customAfter returning to ambient temperature
  2. extractionextracted with ethyl acetate
  3. washThe organic phases are then washed with water
  4. dry with materialwith NaCl solution, dried over calcium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customto be isolated

Sources & evidence

ORD record
ord-32b71274d14b45e5a51ed695cffb70db
Source dataset
uspto-grants-2001_10
Patent number
US06302837B1

Reaction notes

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