Sodium dicyanamide → HCID 178512369, compound

HRID 1492984Notes

Reaction equation

HRID 1492984 reaction equation
Cl.[Cl:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:10]=1[Cl:11])[CH2:6][NH2:7].[N-:12]([C:15]#[N:16])[C:13]#[N:14].[Na+]>C(#N)C>[Cl:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:10]=1[Cl:11])[CH2:6][NH:7][C:15]([NH:12][C:13]#[N:14])=[NH:16]

Participants

4

Reactant 2

HCID 4350929Sodium dicyanamideHCID 448907993,4-Dichlorobenzylamine hydrochloride

Product 1

HCID 178512369HCID 178512369, compoundYield 79.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Putting 63.7 g (300 mM) of 3,4-dichlorobenzylamine hydrochloride and 30.9 g (1.1 eq.) of sodium dicyanamide in 950 ml (15 V) of acetonitrile, the mixture was heated and refluxed for 3.5 hours. Distilling away the solvent, 600 ml of water was added to the residue (white solid) to disperse and wash. Obtained crystals were filtered off, and dispersed and washed in 600 ml of dichloromethane. Since residue of amine was recognized, the crystals were dispersed and washed again in 600 ml of water and 500 ml of dichloromethane. Crystals were filtered off, and dried overnight at 60° C., and 57.7 g (78.9%) of the captioned compound was obtained.

Workup

  1. temperaturethe mixture was heated
  2. temperaturerefluxed for 3.5 hours
  3. distillationDistilling away the solvent, 600 ml of water
  4. additionwas added to the residue (white solid)
  5. additionto disperse
  6. washwash
  7. customObtained crystals
  8. filtrationwere filtered off
  9. additiondispersed
  10. washwashed in 600 ml of dichloromethane
  11. additionthe crystals were dispersed
  12. washwashed again in 600 ml of water
  13. filtrationCrystals were filtered off
  14. customdried overnight at 60° C.

Sources & evidence

ORD record
ord-ca66f2f607c74df387ae0486c3b87786
Source dataset
uspto-grants-1994_12
Patent number
US05376686

Reaction notes

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