Hydrochloric Acid → DE(2-chloro)-4-chloro-icerguastat

HRID 2099517Notes

Reaction equation

HRID 2099517 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[CH:4][CH:3]=1.Cl.C(=O)(O)O.[NH2:15][NH:16][C:17]([NH2:19])=[NH:18].[OH-].[K+]>>[Cl:1][C:2]1[CH:9]=[CH:8][C:5](/[CH:6]=[N:15]/[NH:16][C:17](=[NH:18])[NH2:19])=[CH:4][CH:3]=1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 77264-ChlorobenzaldehydeHCID 14797Potassium HydroxideHCID 178513185HCID 178513185, compound

Product 1

HCID 178513142DE(2-chloro)-4-chloro-icerguastatYield 88.2%

Procedure

A mixture of 4-chlorobenzaldehyde (2.0 g, 10.2 mmol), 20% hydrochloric acid (4 mL) was added to an aminoguanidine bicarbonate (1.39 g, 10.2 mmol) aqueous solution, and heated to reflux for 4 h. A solution of 40% aqueous potassium hydroxide (7 mL) was added dropwise, the mixture was heated at reflux for 10 min and the precipitate formed. The precipitate was filtered, washed with water, and recrystallized from ethanol to give 2-[(E)-1-(4-chlorophenyl)methylidene]-1-hydrazinecarboximidamide (1.77 g, 88%) as a yellow solid.

Workup

  1. temperatureheated
  2. temperatureto reflux for 4 h
  3. temperaturethe mixture was heated
  4. temperatureat reflux for 10 min
  5. customthe precipitate formed
  6. filtrationThe precipitate was filtered
  7. washwashed with water
  8. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-0aa81e304c9e4806be287f7265657097
Source dataset
uspto-grants-2009_08
Patent number
US07569596B2

Reaction notes

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