Acetic Acid → (+/-)-6-fluoro-8-acetamido-2,3-dihydrospiro[4H-1-benzopyran-4,5'-thiazolidine]-2',4'-dione

HRID 279878Notes

Reaction equation

HRID 279878 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([NH2:18])[C:5]2[O:17][CH2:16][CH2:15][C:8]3([S:12][C:11](=[O:13])[NH:10][C:9]3=[O:14])[C:6]=2[CH:7]=1.[C:19](O)(=[O:21])[CH3:20]>C(OC(=O)C)(=O)C>[F:1][C:2]1[CH:3]=[C:4]([NH:18][C:19](=[O:21])[CH3:20])[C:5]2[O:17][CH2:16][CH2:15][C:8]3([S:12][C:11](=[O:13])[NH:10][C:9]3=[O:14])[C:6]=2[CH:7]=1

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 13998518(+/-)-6-Fluoro-8-amino-2,3-dihydrospiro[4H-1-benzopyran-4,5'-thiazolidine]-2',4'-dione

Product 1

HCID 13998520(+/-)-6-fluoro-8-acetamido-2,3-dihydrospiro[4H-1-benzopyran-4,5'-thiazolidine]-2',4'-dione

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Procedure

61 mg of (±)-6-fluoro-8-amino-2,3-dihydrospiro[4H-1-benzopyran-4,5'-thiazolidine]-2',4'-dione were heated to 50° C. for 90 minutes in a mixture of 1.2 ml of glacial acetic acid and 1.2 ml of acetic acid anhydride and the resulting mixture was subsequently concentrated to dryness in vacuo. After boiling up briefly with active carbon in methanolic solution, the residue was crystallized from methanol and yielded (±)-6-fluoro-8-acetamido-2,3-dihydrospiro[4H-1-benzopyran-4,5'-thiazolidine]-2',4'-dione in the form of a light brownish material of melting point 278°-280° C.

Workup

  1. concentrationthe resulting mixture was subsequently concentrated to dryness in vacuo
  2. customthe residue was crystallized from methanol

Sources & evidence

ORD record
ord-9d6c86e04b5f47acb7d2e49a2afcb272
Source dataset
uspto-grants-1986_05
Patent number
US04587256

Reaction notes

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