Ammonium → HCID 22939370, compound

HRID 748366Notes

Reaction equation

HRID 748366 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-39b68aa50f7040d9a37bdef424aca9db
Source dataset
uspto-grants-2008_07
Patent number
US07399759B2

Reaction notes

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