Sodium dicyanamide → HCID 178443243, compound

HRID 1285326Notes

Reaction equation

HRID 1285326 reaction equation
Cl.Cl.[CH2:3]([NH:15][CH2:16][CH2:17][CH2:18][NH2:19])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14].[N-:20]([C:23]#[N:24])[C:21]#[N:22].[Na+]>C(O)CCC>[C:21]([NH:20][C:23](=[NH:24])[NH:19][CH2:18][CH2:17][CH2:16][N:15]([CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])[C:23]([NH:20][C:21]#[N:22])=[NH:24])#[N:22]

Participants

4

Reactant 2

HCID 4350929Sodium dicyanamideHCID 20248914HCID 20248914, compound

Product 1

HCID 178443243HCID 178443243, compound

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

3-Dodecylaminopropylamine dihydrochloride (15 g.) sodium dicyanamide (9.47 g.) and butanol (250 ml.) were heated under reflux for 4 hours. The mixture was allowed to cool, and filtered, and the solvent was evaporated under reduced pressure. The residue was suspended in toluene and evaporated to small volume under reduced pressure to yield a pale oil, which was purified by chromatography on silica gel, using a gradient elution of isopropanol/methylene dichloride starting at 1:9, and then eluting the required product using a ratio of 1:4. The product 1-(3-cyano-guanidino)-3-(3-cyano-1-dodecylguanidino)propane was obtained as a solid m.p. 126°-129°.

Workup

  1. temperatureunder reflux for 4 hours
  2. temperatureto cool
  3. filtrationfiltered
  4. customthe solvent was evaporated under reduced pressure
  5. customevaporated to small volume under reduced pressure
  6. customto yield a pale oil, which
  7. customwas purified by chromatography on silica gel
  8. washa gradient elution of isopropanol/methylene dichloride starting at 1:9
  9. washeluting the required product

Sources & evidence

ORD record
ord-c2e1a612570f47599217268b60679f3d
Source dataset
uspto-grants-1986_01
Patent number
US04567174

Reaction notes

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