Water → N-(1,3-diamino-1-oxo-3-thioxopropan-2-yl)-2,6-dimethylisonicotinamide

HRID 1771137Notes

Reaction equation

HRID 1771137 reaction equation
[NH2:1][C:2](=[O:17])[CH:3]([NH:6][C:7](=[O:16])[C:8]1[CH:13]=[C:12]([CH3:14])[N:11]=[C:10]([CH3:15])[CH:9]=1)[C:4]#[N:5].[H-].[SH2:19].[Na+].Cl.C(NCC)C.O>O.O1CCOCC1>[NH2:1][C:2](=[O:17])[CH:3]([NH:6][C:7](=[O:16])[C:8]1[CH:9]=[C:10]([CH3:15])[N:11]=[C:12]([CH3:14])[CH:13]=1)[C:4]([NH2:5])=[S:19]

Participants

6

Reactant 4

HCID 962WaterHCID 10197650Diethylammonium chlorideHCID 71060853N-(2-amino-1-cyano-2-oxoethyl)-2,6-dimethylisonicotinamideHCID 86720088Sodium hydrogen sulfide hydride

Product 1

HCID 86720087N-(1,3-diamino-1-oxo-3-thioxopropan-2-yl)-2,6-dimethylisonicotinamideYield 64%

Reagents, catalysts & solvents 1

HCID 218864351,4-Dioxane--water (1/1)Solvent

Conditions

Temperature
60 °C

Procedure

A mixture of N-(2-amino-1-cyano-2-oxoethyl)-2,6-dimethylisonicotinamide (1.5 g, 0.00646 mol, 1 eq), sodium hydrogen sulfide hydride (1.05 g, 0.00646 mol, 3 eq) in water/1,4-dioxane, diethyl amine hydrochloride (1.0 g, 0.01939 mol, 3 eq) is stirred for 14 h at 60° C. After the completion of the reaction, the reaction mass is allowed to cool, water is added and extracted with ethyl acetate and dried over sodium sulfate. The solvent is evaporated and the crude is recrystallised in diethyl ether to afford 1.0 g of N-(1,3-diamino-1-oxo-3-thioxopropan-2-yl)-2,6-dimethylisonicotinamide; yield: 64%; MS (ESI+): 267;

Workup

  1. customAfter the completion of the reaction
  2. temperatureto cool
  3. extractionextracted with ethyl acetate
  4. dry with materialdried over sodium sulfate
  5. customThe solvent is evaporated
  6. customthe crude is recrystallised in diethyl ether

Sources & evidence

ORD record
ord-f12e9637590c46fa805d716f0b27060a
Source dataset
uspto-grants-2016_02
Patent number
US09249114B2

Reaction notes

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