Sodium Hydroxide → 1-(p-Trifluoromethylbenzyl)-5-i-propylbiguanide dihydrochloride

HRID 1973116

Reaction equation

HRID 1973116 reaction equation
[ClH:1].[F:2][C:3]([F:13])([F:12])[C:4]1[CH:11]=[CH:10][C:7]([CH2:8][NH2:9])=[CH:6][CH:5]=1.[CH:14]([NH:17][C:18]([NH:20][C:21]#[N:22])=[NH:19])([CH3:16])[CH3:15].[OH-].[Na+]>O>[ClH:1].[ClH:1].[F:2][C:3]([F:12])([F:13])[C:4]1[CH:11]=[CH:10][C:7]([CH2:8][NH:9][C:21]([NH:20][C:18]([NH:17][CH:14]([CH3:16])[CH3:15])=[NH:19])=[NH:22])=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 160903514-(Trifluoromethyl)benzylamine HydrochlorideHCID 178457589HCID 178457589, compound

Product 1

HCID 1784575911-(p-Trifluoromethylbenzyl)-5-i-propylbiguanide dihydrochloride

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A stirred mixture of 6.9 g (0.035 mole) of p-trifluoromethylbenzylamine hydrochloride and 4.3 (0.035 mole) of 1-i-propyl-3-cyanoguanidine is immersed in a 180° C oil bath for 1 hour. The melt is cooled and dissolved in 35 ml of hot water. The solution is cooled in an ice bath, made alkaline with 40% sodium hydroxide solution, and extracted with 150 ml of ether. The ether layer is dried over potassium carbonate, filtered and the ether solution made strongly acidic with a saturated ethereal hydrochloric acid solution. The precipitate is washed twice with 25 ml of anhydrous ether and recrystallized from a mixture of ethanol and heptane (3:5) to obtain 1-(p-trifluoromethylbenzyl)-5-i-propylbiguanide dihydrochloride.

Workup

  1. customis immersed in a 180° C
  2. customfor 1 hour
  3. temperatureThe melt is cooled
  4. temperatureThe solution is cooled in an ice bath
  5. extractionextracted with 150 ml of ether
  6. dry with materialThe ether layer is dried over potassium carbonate
  7. filtrationfiltered
  8. washThe precipitate is washed twice with 25 ml of anhydrous ether
  9. customrecrystallized from a mixture of ethanol and heptane (3:5)

Sources & evidence

ORD record
ord-6642f07e15244849b08bd6e1fa69b90e
Source dataset
uspto-grants-1976_12
Patent number
US03996232

Linked notes

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