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

HRID 2250976

反応式

HRID 2250976 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-8ab7c9e5c76a4497952039a3f3276ff2
出典データセット
uspto-grants-2008_01
特許番号
US07319083B2

関連ノート

読み込み中…