Sodium methanethiolate → HCID 59830764, compound

HRID 1187363Notes

Reaction equation

HRID 1187363 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-64ce086a502e4e758fe756b916234093
Source dataset
uspto-grants-2014_03
Patent number
US08673938B2

Reaction notes

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