Sodium Chloride → HCID 11679942, compound

HRID 1626475Notes

Reaction equation

HRID 1626475 reaction equation
[C:1]([CH:3]([C:8]1[C:13]([Cl:14])=[CH:12][C:11]([Cl:15])=[CH:10][N:9]=1)C(OC)=O)#[N:2].[Cl-].[Na+]>CS(C)=O.O>[Cl:14][C:13]1[C:8]([CH2:3][C:1]#[N:2])=[N:9][CH:10]=[C:11]([Cl:15])[CH:12]=1

Participants

5

Reactant 2

HCID 5234Sodium ChlorideHCID 67288378HCID 67288378, compound

Product 1

HCID 11679942HCID 11679942, compoundYield 76.4%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
130 °C

Procedure

Methyl 2-cyano-2-(3,5-dichloropyridin-2-yl)acetate (120 mg, 0.490 mmol) was diluted with DMSO (1 mL) and water (40 uL) followed by the addition of sodium chloride (14.3 mg, 0.245 mmol). The reaction was heated to 130° C. and stirred for 3 hours. The reaction was allowed to cool, loaded onto silica gel and eluted with 5% ethyl acetate/hexanes to 50% ethyl acetate/hexanes to yield the desired compound (70 mg, 0.374 mmol, 76.4% yield).

Workup

  1. temperatureto cool
  2. washeluted with 5% ethyl acetate/hexanes to 50% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-39d1344d703445c3abb421d45ea2406c
Source dataset
uspto-grants-2014_07
Patent number
US08785445B2

Reaction notes

Loading…