Triethylamine → HCID 58515970, compound

HRID 717832Notes

Reaction equation

HRID 717832 reaction equation
[Cl:1][C:2]1[N+:11]([O-])=[CH:10][C:9]([Cl:13])=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[CH2:14]([N:16](CC)CC)C.C[Si](C#N)(C)C>C(#N)C>[Cl:1][C:2]1[N:11]=[C:10]([C:14]#[N:16])[C:9]([Cl:13])=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 82115Trimethylsilyl cyanideHCID 58515933HCID 58515933, compound

Product 1

HCID 58515970HCID 58515970, compoundYield 84.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
70 °C

Procedure

Methyl 2,5-dichloronicotinate 1-oxide (16 g, 72 mmol) was dissolved in acetonitrile (200 mL) with triethylamine (15 mL, 110 mmol) and trimethylsilyl cyanide (24 mL, 180 mmol) was added. The mixture was heated to 70° C. for 30 minutes. Evaporation and purification on silica gel using ethyl acetate in hexanes (0-30%) gave the desired compound (14 g, 82%). LCMS calculated for C8H5Cl2N2O2 (M+H)+: m/z=231.0. found: 230.8.

Workup

  1. additionwas added
  2. customEvaporation and purification on silica gel

Sources & evidence

ORD record
ord-618b9b8c05174c1da84a1c9fd6469148
Source dataset
uspto-grants-2015_11
Patent number
US09193721B2

Reaction notes

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