m-ethylphenyl-N-methylcyanamide → HCID 9858146, compound

HRID 744745Notes

Reaction equation

HRID 744745 reaction equation
[CH2:1]([C:3]1[CH:4]=[C:5]([N:9]([CH3:12])[C:10]#[N:11])[CH:6]=[CH:7][CH:8]=1)[CH3:2].Cl.[CH3:14][NH:15][C:16]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH:19]=[CH:18][CH:17]=1>>[CH2:1]([C:3]1[CH:4]=[C:5]([N:9]([CH3:12])[C:10]([N:15]([CH3:14])[C:16]2[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[CH:19]=[CH:18][CH:17]=2)=[NH:11])[CH:6]=[CH:7][CH:8]=1)[CH3:2]

Participants

3

Reactant 2

HCID 10103434m-ethylphenyl-N-methylcyanamideHCID 21191510N-Methylnaphthalen-1-amine--hydrogen chloride (1/1)

Product 1

HCID 9858146HCID 9858146, compound

Procedure

In a 5 ml round bottom flask was placed N-(3-ethyl phenyl)-N-methylcyanamide (340 mg, 2.18 mmol), N-methyl -1-naphthyl amine hydrochloride (440 mg, 2.28 mmol) and a stir bar. The flask was evacuated via aspirator and flushed with N2. This was immediately placed in a preheated 160° C. oil bath and allowed to stir under N2 for 14 h. The resultant brown glass was dissolved in methanol (5 ml) and diluted with hot distilled water (20 ml). This solution was basified with 0.1N NaOH (25 ml) and extracted with CHCl3 (5×20 ml) to yield a brown oil upon drying (540 mg). A TLC of this brown oil showed a mixture of reactants and product. Reactants were eluted by column chromatography with benzene. The product was eluted with benzene/EtOH 2:1 (TLC Rf=0.09, CHCl3 :EtOH, 1:1) to afford a pale yellow oil, 380 mg (56%). IR (neat) 3323 (--NH), 1690-1570 (broad, --C=NH). 1H-NMR (CDCl3) δ1.02 (t, 3H, J=7.5), 2.35 (q, 2H, J=7.5), 2.96 (s, 3H), 3.27 (s, 3H), 5.70 (broad s, 1H), 6.45-7.73 (m, 11H, H-aromat). 13C-NMR (CDCl3)CN3, 163.4; Ar, 145.9, 144.4, 142.5, 134.0, 129.7, 128.2, 127.8, 125.9, 125.5, 125.3, 125.1, 123.6, 123.1, 123.0, 122.5, 120.8; NCH3, 40.1;N'CH3, 39.4; CH2, 28.2; CH3, 15.0. Mass Spec. m/e calcd for C21H23N3, 317.1892, Found, 317.1881.

Workup

  1. customIn a 5 ml round bottom flask was placed
  2. customThe flask was evacuated via aspirator
  3. customflushed with N2
  4. customThis was immediately placed in a preheated 160° C.
  5. dissolutionThe resultant brown glass was dissolved in methanol (5 ml)
  6. additiondiluted
  7. distillationwith hot distilled water (20 ml)
  8. extractionextracted with CHCl3 (5×20 ml)
  9. customto yield a brown oil
  10. customupon drying (540 mg)
  11. additiona mixture of reactants and product
  12. washReactants were eluted by column chromatography with benzene
  13. washThe product was eluted with benzene/EtOH 2:1 (TLC Rf=0.09, CHCl3 :EtOH, 1:1)
  14. customto afford a pale yellow oil, 380 mg (56%)

Sources & evidence

ORD record
ord-cba04f8a9edc41608e9db95c453cd66d
Source dataset
uspto-grants-1996_09
Patent number
US05559154

Reaction notes

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