Pyridine → HCID 178475435, compound

HRID 2286500Notes

Reaction equation

HRID 2286500 reaction equation
[SH:1][C:2]1[C:7]([OH:8])=[CH:6][CH:5]=[CH:4][N:3]=1.[C:9](OC(=O)C)(=[O:11])[CH3:10].N1C=CC=CC=1>O1CCCC1>[C:9]([O:8][C:7]1[C:2]([SH:1])=[N:3][CH:4]=[CH:5][CH:6]=1)(=[O:11])[CH3:10]

Participants

5

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 178516238HCID 178516238, compound

Product 1

HCID 178475435HCID 178475435, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-Mercapto-3-pyridinol (25) (1.27 g) was dissolved in tetrahydrofuran (50 ml) and treated with acetic anhydride (2 ml) and pyridine (1 ml). The reaction was stirred at room temperature for 48 hours, the solvent evaporated and the residue chromatographed on silica H [Merck Kieselgel 60 (>230 mesh)] to yield 3-acetoxy-2-mercaptopyridine (26) as a yellow crystalline solid from ethyl acetate (0.9 g) m.p. 178°-80°; νmax (CHCl3) 3400, 1760, 1605, 1590, 1460, 1180 cm-1 ; δ (CDCl3 +DMSO-d6) 2.36 (3H, s, COCH3) 6.80 (1H, dd, J18, 20 Hz, CS-H), 7.18 (1H, d) and 7.60 (1H, d,) C4 and C6 H's (Found: C, 49.77; H, 4.16; N, 8.36. C7H7NO2S requires C, 49.70; H, 4.14; N, 8.28%).

Workup

  1. customthe solvent evaporated
  2. customthe residue chromatographed on silica H [Merck Kieselgel 60 (>230 mesh)]

Sources & evidence

ORD record
ord-75b9581464e74bc9aeaf0374a6ec5ac9
Source dataset
uspto-grants-1981_05
Patent number
US04267177

Reaction notes

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