Formic Acid → 2,6-Bis[1-(4-allyl-2,6-diisopropylphenylimino)ethyl]pyridine

HRID 2250976

반응식

HRID 2250976 반응식
[C:1]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([C:10](=O)[CH3:11])[N:5]=1)(=O)[CH3:2].[CH2:13]([C:16]1[CH:22]=[C:21]([CH:23]([CH3:25])[CH3:24])[C:19]([NH2:20])=[C:18]([CH:26]([CH3:28])[CH3:27])[CH:17]=1)[CH:14]=[CH2:15].C(O)=O>CO>[CH2:13]([C:16]1[CH:17]=[C:18]([CH:26]([CH3:28])[CH3:27])[C:19]([N:20]=[C:1]([C:4]2[CH:9]=[CH:8][CH:7]=[C:6]([C:10](=[N:20][C:19]3[C:21]([CH:23]([CH3:24])[CH3:25])=[CH:22][C:16]([CH2:13][CH:14]=[CH2:15])=[CH:17][C:18]=3[CH:26]([CH3:28])[CH3:27])[CH3:11])[N:5]=2)[CH3:2])=[C:21]([CH:23]([CH3:24])[CH3:25])[CH:22]=1)[CH:14]=[CH2:15]

참가 물질

5

반응물 3

HCID 284Formic AcidHCID 707902,6-DiacetylpyridineHCID 219306712,6-Di(propan-2-yl)-4-(prop-2-en-1-yl)aniline

생성물 1

HCID 865938702,6-Bis[1-(4-allyl-2,6-diisopropylphenylimino)ethyl]pyridine

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

A solution containing 2,6-diacetylpyridine (0.30 g, 1.84 mmol), 4-allyl-2,6-diisopropylaniline (0.80 g, 3.68 mmol), and formic acid (2 ml) in 30 ml dry methanol was refluxed under argon for 14 hours. Yellow solid was collected by filtration and washed with cold methanol (3×5 ml). Recrystallization from CH2Cl2:hexane (1:4) yielded 0.70 g (68%) of yellow, 2,6-bis[1-(4-allyl-2,6-diisopropylphenylimino)ethyl]pyridine crystals. IR (KBr): v(C═N) 1639 cm−1. 1H-NMR (CDCl3): 8.47(d, 2H, Py-Hm), 7.92(t, 1H, Py-Hp), 6.98(s, 4H, Ph-Hm), 6.04(m, 2H, CH═C), 5.12(m, 4H, C═CH2), 3.40(d, 4H, CH2—C═C), 2.75(m, 4H, CH(Me)2), 2.27(s, 6H, CH3), 1.15(d, 24H, C(CH3)2); 13C-NMR(CDCl3): 167.04(C═N), 155.15(Py-C), 144.57(Ph-C), 138.12(Ph-C), 136.79(Py-C), 135.69(Ph-C), 134.75(—CH═), 123.16(Py-C), 122.12(Ph-C), 115.34(═CH2), 40.25(—CH2—), 28.31(C(Me)2), 23.24(CH3), 22.92(CH3), 17.14(CH3). C39H51N3 (561.86 g·mol-1): Anal. Calcd: C, 83.37; H, 9.15; N, 7.48. Found: C, 83.03; H, 9.13; N, 7.55.

후처리

  1. temperaturewas refluxed under argon for 14 hours
  2. filtrationYellow solid was collected by filtration
  3. washwashed with cold methanol (3×5 ml)
  4. customRecrystallization from CH2Cl2:hexane (1:4)

출처 및 근거

ORD 기록
ord-8ab7c9e5c76a4497952039a3f3276ff2
출처 데이터셋
uspto-grants-2008_01
특허 번호
US07319083B2

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