Sulfuric Acid → HCID 4870887, compound

HRID 912646Notes

Reaction equation

HRID 912646 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][NH:8][C:9]([NH2:11])=[S:10].[C:12]([CH2:14][C:15](OCC)=[O:16])#[N:13].[O-]CC.[Na+].[Na].S(=O)(=O)(O)O>C(O)C.O>[NH2:13][C:12]1[N:8]([CH2:7][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=2)[C:9](=[S:10])[NH:11][C:15](=[O:16])[CH:14]=1

Participants

8

Reactant 5

HCID 1118Sulfuric AcidHCID 7764Ethyl cyanoacetateHCID 2723922Sodium ethoxideHCID 5360545SodiumHCID 18399976HCID 18399976, compound

Product 1

HCID 4870887HCID 4870887, compoundYield 96%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

N-(Pyridin-2-ylmethyl)thiourea (1.35 g, 8.09 mmol, obtained from Example 1(a)) and ethyl cyanoacetate (1.1 g, 9.71 mmol) was added to sodium ethoxide (freshly made from sodium 0.20 g, 8.9 mmol in ethanol (16 mL)). The reaction mixture was stirred under reflux at 90° C. for 16 h. The mixture was then diluted with water (20 mL) and neutralized with 2M sulfuric acid. The precipitated solid was collected by filtration, washed with water and dried, giving the title compound (1.8 g, 96%) as a solid. The crude product was used in the next step without further purification.

Workup

  1. filtrationThe precipitated solid was collected by filtration
  2. washwashed with water
  3. customdried

Sources & evidence

ORD record
ord-6e57f2daee38412a92154aaf45ed33fd
Source dataset
uspto-grants-2011_09
Patent number
US08026244B2

Reaction notes

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