tert-Butyl mercaptan → 2-Tert-butylthio-5-ethyl-6-methyl-3-nitropyridine

HRID 1033001Notes

Reaction equation

HRID 1033001 reaction equation
[H-].[Na+].[CH3:3][C:4]([SH:7])([CH3:6])[CH3:5].Cl[C:9]1[C:14]([N+:15]([O-:17])=[O:16])=[CH:13][C:12]([CH2:18][CH3:19])=[C:11]([CH3:20])[N:10]=1>CN(C)C=O>[C:4]([S:7][C:9]1[C:14]([N+:15]([O-:17])=[O:16])=[CH:13][C:12]([CH2:18][CH3:19])=[C:11]([CH3:20])[N:10]=1)([CH3:6])([CH3:5])[CH3:3]

Participants

5

Reactant 3

HCID 6387tert-Butyl mercaptanHCID 24758Sodium hydrideHCID 103755472-Chloro-5-ethyl-6-methyl-3-nitropyridine

Product 1

HCID 104000932-Tert-butylthio-5-ethyl-6-methyl-3-nitropyridineYield 26.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a suspension of sodium hydride (0.23 g, 9.8 mmol) in dimethylformamide (DMF, 20 mL) under an atmosphere of nitrogen, 2-methyl-2-propanethiol (1 mL, 8 mmol) was added. After stirring at room temperature for 15 minutes, a clear solution was obtained. Then a solution of 2-chloro-5-ethyl-6-methyl-3-nitropyridine (1.5 g, 7.5 mmol) in DMF (2 mL) was added, and the reacting mixture turned dark green to black in color. After addition was completed, the mixture was stirred for an additional 15 minutes, and then concentrated under reduced pressure (0.1 torr). The residue was subjected to column chromatography on silica gel, eluted with 60% chloroform in hexane. Collection and concentration of appropriate fractions yielded 0.5 g (26%) of the corresponding 2-tert-butylthiopyridine as a bright yellow solid.

Workup

  1. customa clear solution was obtained
  2. additionAfter addition
  3. stirringthe mixture was stirred for an additional 15 minutes
  4. concentrationconcentrated under reduced pressure (0.1 torr)
  5. washeluted with 60% chloroform in hexane
  6. customCollection and concentration of appropriate fractions

Sources & evidence

ORD record
ord-b0e7e192c32c446daf88eb873edfa676
Source dataset
uspto-grants-1994_05
Patent number
US05308854

Reaction notes

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