Ammonium → HCID 22939370, compound

HRID 499548Notes

Reaction equation

HRID 499548 reaction equation
[C:1]([C:3]1[N:8]=[C:7]([CH2:9][C:10](O)=[S:11])[CH:6]=[CH:5][CH:4]=1)#[N:2].ClC(OCC(C)C)=O.C([N:23](CC)CC)C.[NH4+]>C(OCC)(=O)C.C1COCC1>[C:1]([C:3]1[N:8]=[C:7]([CH2:9][C:10]([NH2:23])=[S:11])[CH:6]=[CH:5][CH:4]=1)#[N:2]

Participants

7

Reactant 4

HCID 223AmmoniumHCID 8471TriethylamineHCID 62365Isobutyl chloroformateHCID 178509753HCID 178509753, compound

Product 1

HCID 22939370HCID 22939370, compoundYield 56.5%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of (6-cyano-2-pyridyl)thioacetic acid (0.95 g, 4.89 mmol), isobutyl chloroformate (1.05 ml, 7.33 mmol), triethylamine (1.03 ml, 7.33 mmol) and THF (150 ml) was stirred under ice cooling condition for 2 hrs. 28% ammonium solution (100 ml) was added to the mixture, and the mixture was stirred under ice cooling condition for 2 hrs. The reaction mixture was combined with ethyl acetate. The organic layer was washed with saturated brine and dried over magnesium sulfate. The solvent was evaporated to give the titled compound (0.49 g, 52%) as pale yellow crystals

Workup

  1. stirringthe mixture was stirred under ice cooling condition for 2 hrs
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over magnesium sulfate
  4. customThe solvent was evaporated

Sources & evidence

ORD record
ord-e408501d354848f5b781d046fffc2947
Source dataset
uspto-grants-2010_08
Patent number
US07767665B2

Reaction notes

Loading…