Thionyl Chloride → 5-[3-(1-chloroethyl)-6-cyano-2-ethoxy-5-methylphenyl]-N,N-dimethylpyridine-2-carboxamide

HRID 1499905Notes

Reaction equation

HRID 1499905 reaction equation
S(Cl)([Cl:3])=O.[C:5]([C:7]1[C:12]([CH3:13])=[CH:11][C:10]([CH:14](O)[CH3:15])=[C:9]([O:17][CH2:18][CH3:19])[C:8]=1[C:20]1[CH:21]=[CH:22][C:23]([C:26]([N:28]([CH3:30])[CH3:29])=[O:27])=[N:24][CH:25]=1)#[N:6]>C(Cl)Cl.CN(C)C=O>[Cl:3][CH:14]([C:10]1[C:9]([O:17][CH2:18][CH3:19])=[C:8]([C:20]2[CH:21]=[CH:22][C:23]([C:26]([N:28]([CH3:30])[CH3:29])=[O:27])=[N:24][CH:25]=2)[C:7]([C:5]#[N:6])=[C:12]([CH3:13])[CH:11]=1)[CH3:15]

Participants

5

Reactant 2

HCID 24386Thionyl ChlorideHCID 866778275-[2-Cyano-6-ethoxy-5-(1-hydroxyethyl)-3-methylphenyl]-N,N-dimethylpyridine-2-carboxamide

Product 1

HCID 866778285-[3-(1-chloroethyl)-6-cyano-2-ethoxy-5-methylphenyl]-N,N-dimethylpyridine-2-carboxamideYield 91%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent2×

Procedure

Thionyl chloride (900 μL, 10 mmol) was added dropwise to a solution of 5-[2-cyano-6-ethoxy-5-(1-hydroxyethyl)-3-methylphenyl]-N,N-dimethylpyridine-2-carboxamide (2.3 g, 6.5 mmol) in methylene chloride (100 mL) and N,N-dimethylformamide (100 μL) at room temperature. The reaction was stirred for 3 hrs, was diluted with methylene chloride (100 mL) and washed with water saturated NaHCO3. The combined organic layer was washed with brine, dried over MgSO4, filtered and concentrated to give crude 5-[3-(1-chloroethyl)-6-cyano-2-ethoxy-5-methylphenyl]-N,N-dimethylpyridine-2-carboxamide (2.2 g, 91%). LCMS calculated for C20H23ClN3O2(M+H)+: m/z=372.1; found: 372.2.

Workup

  1. washwashed with water saturated NaHCO3
  2. washThe combined organic layer was washed with brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-34949857e5dc4334bac66f911f734ace
Source dataset
uspto-grants-2015_12
Patent number
US09199982B2

Reaction notes

Loading…