Water → 2-t-Butylthio-3-cyano-5-ethylpyridine

HRID 1033012Notes

Reaction equation

HRID 1033012 reaction equation
[C:1]([SH:5])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].Cl[C:9]1[C:14]([C:15]#[N:16])=[CH:13][C:12]([CH2:17][CH3:18])=[C:11](C)[N:10]=1.O>CN(C)C=O>[C:1]([S:5][C:9]1[C:14]([C:15]#[N:16])=[CH:13][C:12]([CH2:17][CH3:18])=[CH:11][N:10]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 6387tert-Butyl mercaptanHCID 24758Sodium hydrideHCID 101037782-Chloro-3-cyano-5-ethyl-6-methylpyridine

Product 1

HCID 190862522-t-Butylthio-3-cyano-5-ethylpyridineYield 98%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

t-Butylmercaptan (0.40 mL, 3.55 mmol) was added to a suspension of 60% sodium hydride in mineral oil (158 mg, 3.85 mmol) in dry dimethylformamide (5 mL). After 10 minutes, when gas evolution ceased, 2-chloro-3-cyano-5-ethyl-6-methylpyridine (542 mg, 3.0 mmol) was added. After stirring for one hour, water was added and product extracted into diethyl ether. This extract was dried (Na2SO4), filtered and the solvent removed to give 648 mg (92%) of crystalline product, m.p. 63°-66° C.

Workup

  1. extractionproduct extracted into diethyl ether
  2. dry with materialThis extract was dried (Na2SO4)
  3. filtrationfiltered
  4. customthe solvent removed

Sources & evidence

ORD record
ord-027422d4559a4d4d8323ce7b1464c43f
Source dataset
uspto-grants-1994_05
Patent number
US05308854

Reaction notes

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