Nitrogen → HCID 20138518, compound

HRID 236453Notes

Reaction equation

HRID 236453 reaction equation
N#N.C([S:6][CH2:7][C:8]1[CH:13]=[CH:12][N:11]=[C:10]([CH3:14])[CH:9]=1)(=O)C>>[SH:6][CH2:7][C:8]1[CH:13]=[CH:12][N:11]=[C:10]([CH3:14])[CH:9]=1

Participants

3

Reactant 2

HCID 947NitrogenHCID 20138537HCID 20138537, compound

Product 1

HCID 20138518HCID 20138518, compoundYield 96%

Conditions

Temperature
0 °C

Procedure

To 15 mL of ice-cold, N2 -purged 1N NaOH was added all at once 4-(acetylthiomethyl)-2-methylpyridine (1.358 g, 0.0075 mol). After stirring for 15 min at 0° C. the reaction mixture was washed with ether (2×5 mL), neutralized with concentrated HCl and extracted with methylene chloride (3×10 mL). Evaporation of the methylene chloride solution afforded the thiol (0.89 g, 96%) as a pale yellow oil which gradually became pink on standing: 1Hnmr (CDCl3) δ8.43, 7.37 (ABq, J=5 Hz, 2H), 7.43 (s, 1H), 3.63 (d, J=7.5 Hz, CH2), 2.55 (s, CH3), 1.81 (t, J=7.5 Hz, SH).

Workup

  1. washwas washed with ether (2×5 mL)
  2. extractionextracted with methylene chloride (3×10 mL)
  3. customEvaporation of the methylene chloride solution

Sources & evidence

ORD record
ord-9a3eb61e8ae34819af0b1983380a3bb9
Source dataset
uspto-grants-1987_02
Patent number
US04644061

Reaction notes

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