m-ethylphenyl-N-methylcyanamide → N-(3-Ethylphenyl)-N-methyl-N'-ethyl-N'-(1-naphthyl)guanidine

HRID 1683275Notes

Reaction equation

HRID 1683275 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.[CH2:14]([NH:16][C:17]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH:20]=[CH:19][CH:18]=1)[CH3:15]>>[CH2:1]([C:3]1[CH:4]=[C:5]([N:9]([CH3:12])[C:10]([N:16]([CH2:14][CH3:15])[C:17]2[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[CH:20]=[CH:19][CH:18]=2)=[NH:11])[CH:6]=[CH:7][CH:8]=1)[CH3:2]

Participants

3

Reactant 2

HCID 10103434m-ethylphenyl-N-methylcyanamideHCID 21191491n-Ethyl-1-naphthylamine hydrochloride

Product 1

HCID 9996818N-(3-Ethylphenyl)-N-methyl-N'-ethyl-N'-(1-naphthyl)guanidineYield 71%

Procedure

In a 5 ml round bottom flask was placed N-(3-ethylphenyl)-N-methylcyanamide (626 mg, 3.91 mmol), N-ethyl-N-(1naphthyl)amine hydrochloride (859 mg, 4.15 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 (6 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 brownish green oil (920 mg). A TLC of this oil showed a mixture of reactants and product. Reactants were eluted by column chromatography with benzene. The product was eluted with benzene/EtOH 20:1 (TLC Rf =0.064, CHCl3 :EtOH, 1:1) to afford a pale greenish viscous oil, 460 mg (35.5%). IR (neat) 3484, 3394 (--NH), 1635 (--C=NH). 1H-NMR (CDCl3) δ 1.00 (t, 3H, J=7.5), 1.14 (t, 3H, J=6.6), 2.32 (q, 2H, J=7.5), 2.91 (s, 3H), 3.72 (q, 2H, J=6.6), 5.62 (s, 1H), 6.34-7.73 (m, 11H, H-aromat). 13C-NMR (CDCl3) CN3, 162.2; Ar, 145.9, 144.0, 140.3, 133.7, 130.3, 127.9, 127.5, 125.5, 125.1, 125.0, 124.5, 124.4, 122.7, 122.6, 122.4, 120.4; NCH2, 46.2; NCH3, 39.1; CH2, 27.9; CH3, 14.8; CH3, 12.5. Mass Spec. m/e calcd for C22H25N3, 331.2048, Found, 331.2046.

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 (6 ml)
  6. additiondiluted
  7. distillationwith hot distilled water (20 ml)
  8. extractionextracted with CHCl3 (5×20 ml)

Sources & evidence

ORD record
ord-775b4987d19643b3b24c6bda52115dc5
Source dataset
uspto-grants-1997_06
Patent number
US05637622

Reaction notes

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