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

HRID 482573노트

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HRID 482573 반응식
[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]

참가 물질

3

반응물 2

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

생성물 1

HCID 9858146HCID 9858146, 화합물

실험 절차

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) δ 1.02 (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.

후처리

  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%)

출처 및 근거

ORD 기록
ord-d2f2d198d04748f68938eaede83791a1
출처 데이터셋
uspto-grants-1998_08
특허 번호
US05798390

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