Dimethylformamide → Methyl 3-(3-cyanopyridin-2-ylthio)propanoate

HRID 502592Notes

Reaction equation

HRID 502592 reaction equation
CN(C)C=O.C[O-].[Na+].[SH:9][CH2:10][CH2:11][C:12]([O:14][CH3:15])=[O:13].Cl[C:17]1[C:22]([C:23]#[N:24])=[CH:21][CH:20]=[CH:19][N:18]=1>O>[C:23]([C:22]1[C:17]([S:9][CH2:10][CH2:11][C:12]([O:14][CH3:15])=[O:13])=[N:18][CH:19]=[CH:20][CH:21]=1)#[N:24]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 18050Methyl 3-mercaptopropionateHCID 810792-ChloronicotinonitrileHCID 10942334Sodium Methoxide

Product 1

HCID 13793439Methyl 3-(3-cyanopyridin-2-ylthio)propanoateYield 72%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of anhydrous N,N-dimethylformamide (30 ml), sodium methoxide (0.54 g, 10 mmol), methyl 3-mercaptopropionate (1.20 g, 10 mmol) and 2-chloro-3-cyanopyridine (1.38 g, 10 mmol) was stirred at room temperature for 1 h. The reaction mixture was poured into water (200 ml), the product filtered, washed with water and recrystallized from ethyl acetate/hexanes to yield methyl 3-(3-cyanopyridin-2-ylthio)propanoate (1.60 g). mp 101-102° C. as heavy colorless prisms. 1H NMR (300 MHz, CDCl3): 8.45 (dd, 1H), 7.02 (dd, 1H), 3.68 (s, 3H), 3.49 (t, 2H), 2.78 ppm (t, 2H).

Workup

  1. filtrationthe product filtered
  2. washwashed with water
  3. customrecrystallized from ethyl acetate/hexanes

Sources & evidence

ORD record
ord-629bcbe262c145f8ad2897fcf82fe888
Source dataset
uspto-grants-2010_08
Patent number
US07776847B2

Reaction notes

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