Sodium Hydroxide → Benzamidine

HRID 1380050Notes

Reaction equation

HRID 1380050 reaction equation
Cl.C[C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][CH:11]=1)[C:6]([NH2:8])=[NH:7].[OH-].[Na+]>C(Cl)(Cl)Cl>[C:6]([NH2:8])(=[NH:7])[C:5]1[CH:9]=[CH:10][CH:11]=[CH:3][CH:4]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 28007013-methylbenzenecarboximidamide Hydrochloride

Product 1

HCID 2332Benzamidine

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

A 92.3 g portion of 3-methylbenzamidine, hydrochloride [J. B. Ekeley, et al., J. Am. Chem. Soc., 57, 381 (1935)] was stirred with 200 ml of 5N sodium hydroxide and 400 ml of chloroform for 1/2 hour. When solution was complete the chloroform layer was separated and the aqueous layer extracted twice with 50 ml portions of chloroform. The chloroform solutions were combined, dried over sodium sulfate and evaporated, giving 69.3 g of free benzamidine. This benzamidine was taken up in one liter of absolute ethanol, 71.6 g of ethyl formylacetate sodium salt was added and the mixture was refluxed for 3 days. After cooling, the ethanol was evaporated and the residue dissolved in one liter of water and filtered. The pH of the filtrate was adjusted to 6 with 1N hydrochloric acid and the solid was collected and dried, giving 59.1 g of the desired intermediate as a white solid, mp 148°-149.5° C.

Workup

  1. customwas separated
  2. extractionthe aqueous layer extracted twice with 50 ml portions of chloroform
  3. dry with materialdried over sodium sulfate
  4. customevaporated

Sources & evidence

ORD record
ord-5aaf9edcce2e4fe4b4b5a69a183ad72a
Source dataset
uspto-grants-1986_04
Patent number
US04579848

Reaction notes

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