m-ethylphenyl-N-methylcyanamide → HCID 9858146、化合物

HRID 964168ノート

反応式

HRID 964168 の反応式
[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]

参加物

3

反応物 2

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

生成物 1

HCID 9858146HCID 9858146、化合物

実験手順

In a 5 ml round bottom flask was placed N-(3-ethylphenyl)-N-methylcyanamide (340 mg, 2.18 mmol), N-methyl-1-naphthylamine 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.

後処理

  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%)

出典と根拠

ORDレコード
ord-2d6883112770405f9efb9fc30e507ecf
出典データセット
uspto-grants-1998_06
特許番号
US05767162

反応ノート

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