Acetonitrile → HCID 178464561, compound

HRID 28063Notes

Reaction equation

HRID 28063 reaction equation
[CH2:1]([C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([CH2:9][CH3:10])[C:4]=1[NH:11][C:12]([NH:14][C:15](=N)[NH:16][CH2:17]C)=[O:13])[CH3:2].CO[CH:22](OC)[N:23](C)C.Cl.CO.[CH3:31][C:32]#[N:33]>C(Cl)(Cl)Cl.CO>[CH2:9]([C:5]1[CH:6]=[CH:7][CH:8]=[C:3]([CH2:1][CH3:2])[C:4]=1[N:11]1[CH:17]=[N:16][C:15]([C:22](=[NH:23])[NH:33][CH2:32][CH3:31])=[N:14][C:12]1=[O:13])[CH3:10]

Participants

7

Reactant 4

HCID 6342Acetonitrile2×HCID 78373Dimethylformamide dimethyl acetalHCID 21893726Hydrochloride methanolHCID 178464630HCID 178464630, compound

Product 1

HCID 178464561HCID 178464561, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6212ChloroformSolvent

Procedure

To a magnetically stirred stined suspension of 10/5 g (40 mmol) of 1-(2',6'-diethylphenyl)-3-ethylamidinourea in 10 ml of CH3CN is added 9.52 g (80 mmol) of N,N-dimethylformamide dimethylacetal and another 20 ml of CH3CN. The reaction mixture is heated to reflux at which point all of the solid dissolves. The solution is refluxed for one hour, allowed to cool to ambient temperature and then concentrated in vacuo to yield an off-white solid which is taken up in CHCl3, washed with H2O) (2×50 ml) and saturated aqueous brine (2×25 ml). All aqueous wash layers are combined and back-extracted with CHCl3, (2×25 ml). All organic layers are combined, dried (Na2SO2), filtered and the filtrate concentrated in vacuo to yield a yellow oil. The oil is taken up in MeOH and acidified with HCl/MeOH then concentrated in vacuo.

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureto reflux at which point all of the solid
  3. dissolutiondissolves
  4. temperatureThe solution is refluxed for one hour
  5. concentrationconcentrated in vacuo
  6. customto yield an off-white solid which
  7. washwashed with H2O) (2×50 ml) and saturated aqueous brine (2×25 ml)
  8. extractionback-extracted with CHCl3, (2×25 ml)
  9. dry with materialdried (Na2SO2)
  10. filtrationfiltered
  11. concentrationthe filtrate concentrated in vacuo
  12. customto yield a yellow oil
  13. concentrationthen concentrated in vacuo

Sources & evidence

ORD record
ord-4604028e153449e28076f7f62bacf13c
Source dataset
uspto-grants-1980_09
Patent number
US04225315

Reaction notes

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