Sodium methanethiolate → HCID 59830764, compound

HRID 2424902Notes

Reaction equation

HRID 2424902 reaction equation
[CH3:1][S-:2].[Na+].[CH:4]12[CH2:13][CH:8]3[CH2:9][CH:10]([CH2:12][CH:6]([CH2:7]3)[CH:5]1[NH:14][C:15]([C:17]1[C:18](Cl)=[N:19][C:20]([Cl:23])=[CH:21][CH:22]=1)=[O:16])[CH2:11]2>CC(N(C)C)=O.CCOC(C)=O>[CH:4]12[CH2:13][CH:8]3[CH2:9][CH:10]([CH2:12][CH:6]([CH2:7]3)[CH:5]1[NH:14][C:15]([C:17]1[C:18]([S:2][CH3:1])=[N:19][C:20]([Cl:23])=[CH:21][CH:22]=1)=[O:16])[CH2:11]2

Participants

5

Reactant 2

HCID 4378561Sodium methanethiolateHCID 59830729HCID 59830729, compound

Product 1

HCID 59830764HCID 59830764, compoundYield 58.5%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 31374DimethylacetamideSolvent

Conditions

Temperature
60 °C

Procedure

Sodium thiomethoxide (0.409 g, 5.84 mmol) was added to N-(2-adamantyl)-2,6-dichloro-pyridine-3-carboxamide (2 g, 6.15 mmol) in DMA (10 mL) at 20° C. under nitrogen. The resulting suspension was stirred at 60° C. for 3 hours. The reaction mixture was diluted with EtOAc (100 mL) and washed with water (3×20 mL), and saturated brine (25 mL). The organic layer was dried over MgSO4, filtered and evaporated to afford crude product which was purified by crystallisation from EtOAc/isohexane to afford N-(2-adamantyl)-6-chloro-2-methylsulfanyl-pyridine-3-carboxamide (1.150 g, 55.5%) as a white solid

Workup

  1. washwashed with water (3×20 mL), and saturated brine (25 mL)
  2. dry with materialThe organic layer was dried over MgSO4
  3. filtrationfiltered
  4. customevaporated
  5. customto afford crude product which
  6. customwas purified by crystallisation from EtOAc/isohexane

Sources & evidence

ORD record
ord-4c29750d71144a8789ab267ac3324c96
Source dataset
uspto-grants-2011_06
Patent number
US07964618B2

Reaction notes

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