Propyl mercaptan → HCID 59830614, compound

HRID 1187359Notes

Reaction equation

HRID 1187359 reaction equation
[CH2:1]([SH:4])[CH2:2][CH3:3].[CH:5]12[CH2:14][CH:9]3[CH2:10][CH:11]([CH2:13][CH:7]([CH2:8]3)[CH:6]1[NH:15][C:16]([C:18]1[C:19](Cl)=[N:20][C:21]([Cl:24])=[CH:22][CH:23]=1)=[O:17])[CH2:12]2.C(=O)([O-])[O-].[Na+].[Na+]>CN(C=O)C.CCOC(C)=O>[CH:5]12[CH2:12][CH:11]3[CH2:10][CH:9]([CH2:8][CH:7]([CH2:13]3)[CH:6]1[NH:15][C:16]([C:18]1[C:19]([S:4][CH2:1][CH2:2][CH3:3])=[N:20][C:21]([Cl:24])=[CH:22][CH:23]=1)=[O:17])[CH2:14]2

Participants

6

Reactant 3

HCID 7848Propyl mercaptanHCID 10340Sodium CarbonateHCID 59830729HCID 59830729, compound

Product 1

HCID 59830614HCID 59830614, compoundYield 84%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

Propanethiol (1.45 mL, 16 mmol) was added to N-(2-adamantyl)-2,6-dichloro-pyridine-3-carboxamide (5.2 g, 16 mmol), and sodium carbonate (5.09 g, 48 mmol) in DMF (50 mL) at 20° C. under nitrogen. The resulting suspension was stirred at 60° C. for 3 hours. The reaction mixture was diluted with EtOAc (400 mL) and washed with water (3×50 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-propylsulfanyl-pyridine-3-carboxamide (4.9 g, 84%)

Workup

  1. washwashed with water (3×50 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-1b72db7bea7c40308e702b572b3cac3b
Source dataset
uspto-grants-2014_03
Patent number
US08673938B2

Reaction notes

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