Ethanethiol → HCID 59830636, compound

HRID 2424901Notes

Reaction equation

HRID 2424901 reaction equation
[CH2:1]([SH:3])[CH3:2].[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.C(=O)([O-])[O-].[Na+].[Na+]>CN(C=O)C.CCOC(C)=O>[CH:6]12[CH2:7][CH:8]3[CH2:9][CH:10]([CH2:11][CH:4]([CH2:13]3)[CH:5]1[NH:14][C:15]([C:17]1[C:18]([S:3][CH2:1][CH3:2])=[N:19][C:20]([Cl:23])=[CH:21][CH:22]=1)=[O:16])[CH2:12]2

Participants

6

Reactant 3

HCID 6343EthanethiolHCID 10340Sodium CarbonateHCID 59830729HCID 59830729, compound

Product 1

HCID 59830636HCID 59830636, compoundYield 72.7%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

Ethanethiol (0.433 mL, 5.84 mmol) was added to N-(2-adamantyl)-2,6-dichloro-pyridine-3-carboxamide (2 g, 6.15 mmol), and sodium carbonate (1.955 g, 18.45 mmol) in DMF (12 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 recrystallised from 15% ethyl acetate/hexane to give N-(2-adamantyl)-6-chloro-2-ethylsulfanyl-pyridine-3-carboxamide (1.489 g, 69%)

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 recrystallised from 15% ethyl acetate/hexane

Sources & evidence

ORD record
ord-425f808268774448930db850762057a0
Source dataset
uspto-grants-2011_06
Patent number
US07964618B2

Reaction notes

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