Acetic Anhydride → HCID 86751830, compound

HRID 1956947Notes

Reaction equation

HRID 1956947 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([C:8](=[N:10][O:11][CH2:12][CH2:13][O:14][C:15]2[CH:28]=[CH:27][C:18]([CH2:19][CH:20]3[S:24][C:23](=[O:25])[NH:22][C:21]3=[O:26])=[CH:17][CH:16]=2)[CH3:9])[CH:5]=[CH:6][CH:7]=1.[C:29](OC(=O)C)(=[O:31])[CH3:30]>N1C=CC=CC=1>[C:29]([O:1][C:2]1[CH:3]=[C:4]([C:8](=[N:10][O:11][CH2:12][CH2:13][O:14][C:15]2[CH:28]=[CH:27][C:18]([CH2:19][CH:20]3[S:24][C:23](=[O:25])[NH:22][C:21]3=[O:26])=[CH:17][CH:16]=2)[CH3:9])[CH:5]=[CH:6][CH:7]=1)(=[O:31])[CH3:30]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 86751828HCID 86751828, compound

Product 1

HCID 86751830HCID 86751830, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 0.30 g of 5-(4-{2-[1-(3-hydroxyphenyl)ethylideneaminooxy]ethoxy}benzyl)thiazolidine-2,4-dione (prepared as described in Example 50), 0.092 ml of acetic anhydride and 15 ml of pyridine was stirred at room temperature for 1.5 hours. At the end of this time, the solvent was removed by distillation under reduced pressure, and then the resulting residue was diluted with water and then extracted with ethyl acetate. The extract was washed with 1N aqueous hydrochloric acid and with an aqueous solution of sodium chloride, in that order, after which it was dried over anhydrous magnesium sulfate. The solvent was then removed by distillation under reduced pressure, and the residue was purified by column chromatography through silica gel, using a 1:2 by volume mixture of ethyl acetate and hexane as the eluent, to give 0.23 g of the title compound, melting at 30°-50° C. (softening point).

Workup

  1. customAt the end of this time, the solvent was removed by distillation under reduced pressure
  2. additionthe resulting residue was diluted with water
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed with 1N aqueous hydrochloric acid and with an aqueous solution of sodium chloride, in that order
  5. dry with materialafter which it was dried over anhydrous magnesium sulfate
  6. customThe solvent was then removed by distillation under reduced pressure
  7. customthe residue was purified by column chromatography through silica gel
  8. additionby volume mixture of ethyl acetate and hexane as the eluent

Sources & evidence

ORD record
ord-d42c57cb6b42488bb6bfedd21202cc81
Source dataset
uspto-grants-1998_07
Patent number
US05780490

Reaction notes

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