Acetic Anhydride → HCID 9956228, compound

HRID 1419099Notes

Reaction equation

HRID 1419099 reaction equation
[C:1](OC(=O)C)(=[O:3])[CH3:2].[OH:8][C:9]1[C:34]([CH3:35])=[C:33]([CH3:36])[C:12]2[N:13]([CH3:32])[C:14]([CH2:16][O:17][C:18]3[CH:31]=[CH:30][C:21]([CH2:22][CH:23]4[S:27][C:26](=[O:28])[NH:25][C:24]4=[O:29])=[CH:20][CH:19]=3)=[N:15][C:11]=2[C:10]=1[CH3:37]>>[C:1]([O:8][C:9]1[C:34]([CH3:35])=[C:33]([CH3:36])[C:12]2[N:13]([CH3:32])[C:14]([CH2:16][O:17][C:18]3[CH:31]=[CH:30][C:21]([CH2:22][CH:23]4[S:27][C:26](=[O:28])[NH:25][C:24]4=[O:29])=[CH:20][CH:19]=3)=[N:15][C:11]=2[C:10]=1[CH3:37])(=[O:3])[CH3:2]

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 9867103HCID 9867103, compound

Product 1

HCID 9956228HCID 9956228, compound

Procedure

0.032 ml of acetic anhydride were added at room temperature to a solution of 0.12 g of 5-[4-(5-hydroxy-1,4,6,7-tetramethylbenzimidazol-2-ylmethoxy)benzyl]thiazolidine-2,4-dione (prepared as described in Example 3) in 2 ml of pylidine, and the resulting mixture was stirred for 3 hours, after which it was allowed to stand overnight. At the end of this time, the reaction mixture was freed from the solvent by evaporation under reduced pressure, and the resulting residue was mixed with water. The aqueous mixture was then extracted with ethyl acetate. The extract was washed with water and then with a saturated aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure, after which the solid residue was triturated with diethyl ether and collected by filtration. It was then washed with diethyl ether, to give 0.12 g of the title compound, melting at 250°-253° C.

Workup

  1. waitto stand overnight
  2. customAt the end of this time, the reaction mixture was freed from the solvent by evaporation under reduced pressure
  3. additionthe resulting residue was mixed with water
  4. extractionThe aqueous mixture was then extracted with ethyl acetate
  5. washThe extract was washed with water
  6. dry with materialwith a saturated aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate
  7. customThe solvent was removed by distillation under reduced pressure
  8. customafter which the solid residue was triturated with diethyl ether
  9. filtrationcollected by filtration
  10. washIt was then washed with diethyl ether

Sources & evidence

ORD record
ord-0372216caa9f4d0a934a9cb51320ac9f
Source dataset
uspto-grants-1999_03
Patent number
US05886014

Reaction notes

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