Thiomorpholine → 2-Chloro-4-(4-fluoro-2-methylphenyl)-6-(thiomorpholin-4-yl)pyridine-3-carbonitrile

HRID 131109Notes

Reaction equation

HRID 131109 reaction equation
[C:1]([C:3]1[C:4]([Cl:18])=[N:5][C:6](Cl)=[CH:7][C:8]=1[C:9]1[CH:14]=[CH:13][C:12]([F:15])=[CH:11][C:10]=1[CH3:16])#[N:2].[NH:19]1[CH2:24][CH2:23][S:22][CH2:21][CH2:20]1>CO>[Cl:18][C:4]1[C:3]([C:1]#[N:2])=[C:8]([C:9]2[CH:14]=[CH:13][C:12]([F:15])=[CH:11][C:10]=2[CH3:16])[CH:7]=[C:6]([N:19]2[CH2:24][CH2:23][S:22][CH2:21][CH2:20]2)[N:5]=1

Participants

4

Reactant 2

HCID 67164ThiomorpholineHCID 573550052,6-Dichloro-4-(4-fluoro-2-methylphenyl)pyridine-3-carbonitrile

Product 1

HCID 573550072-Chloro-4-(4-fluoro-2-methylphenyl)-6-(thiomorpholin-4-yl)pyridine-3-carbonitrileYield 88.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Crude 3-cyano-2,6-dichloro-4-(4-fluoro-2-methylphenyl)pyridine, (32.44 g, 115.4 mmol) and 300 mL of methanol were added to a 500-mL, 3-necked flask (equipped with a 25-mL pressure-equilibrating addition funnel/dry N2 adapter, septum with teflon-coated thermocouple, and teflon paddle stirrer/glass shaft). Thiomorpholine (23.0 mL, 25.0 g, 242 mmol, 2.10 equiv) was added dropwise over a period of 22 minutes via the addition funnel, and the resulting mixture was stirred at 20–25° C. for 18 hours. The precipitate was filtered, washed with 30 mL of methanol, and dried to afford 35.47 g (88.4%) of 2-chloro-3-cyano-4-(4-fluoro-2-methylphenyl)-6-(thiomorpholino)pyridine as a beige solid.

Workup

  1. filtrationThe precipitate was filtered
  2. washwashed with 30 mL of methanol
  3. customdried

Sources & evidence

ORD record
ord-9c7910ea963f49559a4185eb16397f10
Source dataset
uspto-grants-2008_06
Patent number
US07384939B2

Reaction notes

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