Sodium Carbonate → HCID 178503297, compound

HRID 1696783Notes

Reaction equation

HRID 1696783 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([C:8]#[N:9])[CH:5]=[C:4]([S:10][CH3:11])[CH:3]=1.Cl.[NH2:13][OH:14].C(=O)([O-])[O-].[Na+].[Na+]>C(O)C.O>[NH3:1].[NH2:1][C:2]1[N:7]=[C:6]([C:8]([NH:13][OH:14])=[NH:9])[CH:5]=[C:4]([S:10][CH3:11])[CH:3]=1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 443297Hydroxyamine hydrochlorideHCID 67273771HCID 67273771, compound

Product 2

HCID 222AmmoniaHCID 178503297HCID 178503297, compoundYield 111.7%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
85 °C

Procedure

To a solution of 0.179 g 6-amino-4-methylsulfanyl-pyridine-2-carbonitrile in 2.7 ml ethanol and 1.3 ml water was added 0.151 g hydroxylamine hydrochloride and 0.344 g sodium carbonate and the mixture was stirred at 85° C. for 1 h. The mixture was charged onto a 10 g kartusche (Varian Chem Elut 12198007) and the product was eluted with ethyl acetate and purified by chromatography on silica gel with dichloromethane:methanol:ammonia=8:2:0.2 to yield 0.120 g of the title compound as white solid. MS (ISP) M+H+=199.0

Workup

  1. additionThe mixture was charged onto a 10 g kartusche (Varian Chem Elut 12198007)
  2. washthe product was eluted with ethyl acetate
  3. custompurified by chromatography on silica gel with dichloromethane

Sources & evidence

ORD record
ord-f51ddf63384d4c99b201c7540f8eec7e
Source dataset
uspto-grants-2012_04
Patent number
US08163778B2

Reaction notes

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