Ethyl cyanoacetate → HCID 178470801, compound

HRID 1756898Notes

Reaction equation

HRID 1756898 reaction equation
[CH2:1]([O:3][C:4](=[O:8])[CH2:5][C:6]#[N:7])[CH3:2].[NH4+].[Cl-].[N-:11]=[N+:12]=[N-:13].[Na+]>CN(C)C=O>[CH2:1]([O:3][C:4](=[O:8])[CH2:5][C:6]1[NH:13][N:12]=[N:11][N:7]=1)[CH3:2]

Participants

5

Reactant 3

HCID 7764Ethyl cyanoacetateHCID 25517Ammonium ChlorideHCID 33557Sodium Azide

Product 1

HCID 178470801HCID 178470801, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of ethylcyanoacetate (20.0 g, 0.177 mol) in dimethylformamide (DMF) (180 mL) was added NH4Cl (10.4 g, 0.19 mol) and sodium azide (12.6 g, 0.19 mol) sequentially. The mixture was heated for 5 hours at 100° C., allowed to cool, and the DMF removed in vacuo. The residue was taken up in water (150 mL), acidified to pH 2 with concentrated HCl, and filtered. The filtrate was cooled to 5° C. and allowed to crystallize. The solid was filtered, dried in vacuo over self-indicating silica gel to give 10.61 g, 42%, mp 124°-129° C.

Workup

  1. temperatureto cool
  2. customthe DMF removed in vacuo
  3. filtrationfiltered
  4. temperatureThe filtrate was cooled to 5° C.
  5. customto crystallize
  6. filtrationThe solid was filtered
  7. customdried in vacuo over self-indicating silica gel
  8. customto give 10.61 g, 42%, mp 124°-129° C.

Sources & evidence

ORD record
ord-bc3d60dada7f4ff1bd34396a5fc6c981
Source dataset
uspto-grants-1995_08
Patent number
US05441975

Reaction notes

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