Ethyl cyanoacetate → HCID 178507963, compound

HRID 912683Notes

Reaction equation

HRID 912683 reaction equation
[NH:1]1[CH:5]=[CH:4][C:3]([CH2:6][NH:7][C:8]([NH2:10])=[S:9])=[N:2]1.[O-]CC.[Na+].[C:15]([CH2:17][C:18](OCC)=[O:19])#[N:16]>>[NH2:16][C:15]1[N:7]([CH2:6][C:3]2[CH:4]=[CH:5][NH:1][N:2]=2)[C:8](=[S:9])[NH:10][C:18](=[O:19])[CH:17]=1

Participants

4

Reactant 3

HCID 7764Ethyl cyanoacetateHCID 2723922Sodium ethoxideHCID 178514164HCID 178514164, compound

Product 1

HCID 178507963HCID 178507963, compoundYield 44%

Conditions

Temperature
5 °C

Procedure

The title compound was prepared in accordance with the general method described in Example 12(b) by using 1-(1H-pyrazol-3-ylmethyl)thiourea (1.39 g, 8.87 mmol obtained from Example 13(a)), sodium ethoxide (21% w/v, 8.62 mL, 26.6 mmol) and ethyl cyanoacetate (2.84 mL, 26.6 mmol) with the exception that it was necessary to maintain the cloudy solution at 5° C. overnight to obtain precipitation (0.87 g, 44% yield).

Workup

  1. customto obtain
  2. customprecipitation (0.87 g, 44% yield)

Sources & evidence

ORD record
ord-74031081cc3b4b559ee51c9c2236bbb1
Source dataset
uspto-grants-2011_09
Patent number
US08026244B2

Reaction notes

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