Acetic Anhydride → HCID 13097119, compound

HRID 1903740Notes

Reaction equation

HRID 1903740 reaction equation
I.C(OC(=O)C)(=O)C.[O:9]=[C:10]1[N:14]([CH2:15][C:16]([O:18]CC)=[O:17])[C:13]2[CH:21]=[C:22]([O:25]C)[CH:23]=[CH:24][C:12]=2[S:11]1.S(=O)(O)[O-].[Na+]>C(O)(=O)C>[O:9]=[C:10]1[N:14]([CH2:15][C:16]([OH:18])=[O:17])[C:13]2[CH:21]=[C:22]([OH:25])[CH:23]=[CH:24][C:12]=2[S:11]1

Participants

6

Reactant 4

HCID 7918Acetic AnhydrideHCID 24841Hydrogen iodideHCID 13097101HCID 13097101, compoundHCID 23665763Sodium Bisulfite

Product 1

HCID 13097119HCID 13097119, compoundYield 75.6%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a mixture of 57% hydriodic acid (50 ml) and acetic anhydride (15 ml) was added a solution of ethyl 2-oxo-5-methoxy-3-benzothiazolineacetate (2.67 g) in acetic acid (15 ml). The reaction mixture was refluxed with stirring for 1.5 hours and then cooled to ambient temperature. To the resultant mixture were added ice-water and a small volume of sodium bisulfite. The mixture was extracted with ethyl acetate. The extract was washed with water, dried over magnesium sulfate and concentrated under reduced pressure to give crystalline 2-oxo-5-hydroxy-3-benzothiazolineacetic acid (1.7 g).

Workup

  1. temperatureThe reaction mixture was refluxed
  2. extractionThe mixture was extracted with ethyl acetate
  3. washThe extract was washed with water
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-e7137c268f0c4854a21222e80583d0a2
Source dataset
uspto-grants-1984_03
Patent number
US04438126

Reaction notes

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