Cyanamide → HCID 178511002, compound

HRID 1253171Notes

Reaction equation

HRID 1253171 reaction equation
Cl.[NH2:2][C:3]1[CH:7]=[N:6][N:5]([CH2:8][CH2:9][CH2:10][CH2:11][C:12]#[N:13])[N:4]=1.[N:14]#[C:15][NH2:16]>CCO>[NH:2]([C:3]1[CH:7]=[N:6][N:5]([CH2:8][CH2:9][CH2:10][CH2:11][C:12]#[N:13])[N:4]=1)[C:15]([NH2:16])=[NH:14]

Participants

4

Reactant 2

HCID 9864Cyanamide2×HCID 20137163HCID 20137163, compound

Product 1

HCID 178511002HCID 178511002, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution 5-(4-amino-1,2,3-triazol-2-yl)valeronitrile hydrochloride (2.01 g.) in EtOH (15 ml.) was treated with cyanamide (0.42 g.) and the solution heated under reflux for 4.5 hours. A further 0.1 g. of cyanamide was added and heating under reflux was continued for 2 hours. The solution was evaporated and the residue basified with ammonia and continuously extracted for 24 hours with EtOAc to give a yellow oil which was purified by medium pressure chromatography using chloroform/MeOH/aqueous ammonia (s.g. 0.880) 8:2:0.1 v/v/v as eluant to give 5-(4-guanidino-1,2,3-triazol-2-yl)valeronitrile as a colourless oil (0.45 g.).

Workup

  1. temperaturethe solution heated
  2. temperatureunder reflux for 4.5 hours
  3. temperatureheating
  4. temperatureunder reflux
  5. customThe solution was evaporated
  6. extractioncontinuously extracted for 24 hours with EtOAc
  7. customto give a yellow oil which
  8. customwas purified by medium pressure chromatography

Sources & evidence

ORD record
ord-ba62dbdfb8574d2a820d624b41ad008b
Source dataset
uspto-grants-1988_05
Patent number
US04748165

Reaction notes

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