Hydrochloric Acid → HCID 178512373, compound

HRID 1734711Notes

Reaction equation

HRID 1734711 reaction equation
[CH2:1]([NH2:9])[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.Cl.[N-:11]([C:14]#[N:15])[C:12]#[N:13].[Na+]>O>[CH2:1]([NH:9][C:14]([NH:11][C:12]#[N:13])=[NH:15])[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 1001PhenethylamineHCID 4350929Sodium dicyanamide

Product 1

HCID 178512373HCID 178512373, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

48.25 g (0.398 moles) of phenethyl amine is charged to a 500 mL three neck round bottom flask equipped with a stirring shaft and a dropping funnel. The flask is cooled in an ice bath as 38.59 g (0.398 moles) of concentrated hydrochloric acid is added dropwise. After the addition of the acid, the ice bath is replaced by a heating mantle and the mixture is heated to 50° C. 37.20 g (0.418 moles) of sodium dicyanamide is added to the flask with stirring. The mixture is heated to 100° C. and stirred for 6.5 hours then cooled in an ice bath. 150 mL of water are added and the white, crystalline precipitate is collected on a Buchner funnel. The product is recrystallized from water yielding 55.5 g of 1-phenethyl-3-cyanoguanidine (74.1% of theoretical) melting point at 111°-112° C.

Workup

  1. customequipped with a stirring shaft and a dropping funnel
  2. additionis added dropwise
  3. additionAfter the addition of the acid
  4. temperatureThe mixture is heated to 100° C.
  5. stirringstirred for 6.5 hours
  6. temperaturethen cooled in an ice bath
  7. customthe white, crystalline precipitate is collected on a Buchner funnel
  8. customThe product is recrystallized from water yielding 55.5 g of 1-phenethyl-3-cyanoguanidine (74.1% of theoretical)
  9. customat 111°-112° C.

Sources & evidence

ORD record
ord-c89468e453fc488d95c1ace4294774c1
Source dataset
uspto-grants-1996_07
Patent number
US05534565

Reaction notes

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