Pyridine → HCID 86740730, compound

HRID 1380541Notes

Reaction equation

HRID 1380541 reaction equation
[OH:1][CH:2]([C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([CH3:25])[N:20]=1)[CH2:3][O:4][C:5]1[CH:18]=[CH:17][C:8]([CH2:9][CH:10]2[S:14][C:13](=[O:15])[NH:12][C:11]2=[O:16])=[CH:7][CH:6]=1.N1C=CC=CC=1.[C:32](OC(=O)C)(=[O:34])[CH3:33]>O>[C:32]([O:1][CH:2]([C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([CH3:25])[N:20]=1)[CH2:3][O:4][C:5]1[CH:6]=[CH:7][C:8]([CH2:9][CH:10]2[S:14][C:13](=[O:15])[NH:12][C:11]2=[O:16])=[CH:17][CH:18]=1)(=[O:34])[CH3:33]

Participants

5

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 9885141HCID 9885141, compound

Product 1

HCID 86740730HCID 86740730, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixed solution of 5-{4-[2-hydroxy-2-(6-methyl-2-pyridyl)ethoxy]benzyl}-2,4-thiazolidinedione (350 mg), pyridine (5 ml) and acetic anhydride (0.2 ml) was allowed to stand at room temperature for 2 days, and then poured in water, followed by extraction with ethyl acetate. The ethyl acetate layer was washed with water, dried (MgSO4) and freed of the solvent. The residue was chromatographed on a silica gel (20 g) column, and elution was effected with benzene-acetone (15:1, V/V) to give 5-{4-[2-acetoxy-2-(6-methyl-2-pyridyl)ethoxy]benzyl}-2,4-thiazolidinedione in the form of an oily substance. Yield of 360 mg (89.8%). IR (neat): 1740, 1690, 1230 cm-1. NMR (CDCl3)δ: 211(3H,s), 2.51(3H,s), 3.02 (1H,dd,J=14 and 9 Hz), 3.41(1H,dd,J=14 and 4 Hz), 4.37(2H,d, J=5 Hz), 4.44(1H,dd,J=9 and 4 Hz), 6.13(1H,t,J=5 Hz), 6.83(2H, d,J=9 Hz), 7.09(2H,d,J=9 Hz), 7.0-7.7(3H,m).

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe ethyl acetate layer was washed with water
  3. dry with materialdried (MgSO4)
  4. customThe residue was chromatographed on a silica gel (20 g) column, and elution

Sources & evidence

ORD record
ord-cb417b67e8a24b91a13606e3672d517b
Source dataset
uspto-grants-1986_04
Patent number
US04582839

Reaction notes

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