3,4-Dimethylpyridine → 3,4-Dimethyl-1-(13-pyridin-3-yl-tridecyl)-pyridinium bromide

HRID 84342

反応式

HRID 84342 の反応式
[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]1[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=1.[N:21]1[CH:26]=[CH:25][C:24]([CH3:27])=[C:23]([CH3:28])[CH:22]=1>>[Br-:1].[CH3:28][C:23]1[CH:22]=[N+:21]([CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]2[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=2)[CH:26]=[CH:25][C:24]=1[CH3:27]

参加物

3

反応物 2

HCID 114173,4-DimethylpyridineHCID 119534943-(13-Bromo-tridecyl)-pyridine

生成物 1

HCID 247811013,4-Dimethyl-1-(13-pyridin-3-yl-tridecyl)-pyridinium bromide収率 60%

実験手順

3-(13-Bromo-tridecyl)-pyridine (1 mmol) was added to 3,4-lutidine (5 ml), and the mixture was heated at 50 C overnight. The excess picoline was removed in a vacuum, and the resulting residue was partitioned between water and ether. The aqueous layer was washed extensively with ether until no 3,4-lutidine was left in the aqueous layer, and then the aqueous layer was extracted with chloroform. The chloroform was removed to afford the product (60%). 1HNMR (300 MHz, CDCl3, ppm), 9.23 (s, 1H), 9.04 (d, J=6.3, 1H), 8.40 (br, 2H), 7.79 (d, J=6.0, 1H), 7.48 (d, 8.1, 1H), 7.18-7.20 (m, 1H), 4.83 (t, J=7.5, 2H), 2.58 (t, J=7.5, 2H), 2.52 (s, 3H), 2.49 (s, 3H), 2.21 (br, 1H), 1.82-2.02 (m, 2H), 1.54-1.62 (m, 2H), 1.15-1.35 (br, 12H). 13CNMR, 157.61, 149.68, 146.92, 143.35, 141.91, 138.45, 138.33, 136.32, 128.65, 123.57, 61.37, 33.31, 32.19, 31.41, 29.85, 29.80, 29.68, 29.41, 26.45, 20.69, 17.40.

後処理

  1. temperaturethe mixture was heated at 50 C overnight
  2. customThe excess picoline was removed in a vacuum
  3. customthe resulting residue was partitioned between water and ether
  4. washThe aqueous layer was washed extensively with ether until no 3,4-lutidine
  5. waitwas left in the aqueous layer
  6. extractionthe aqueous layer was extracted with chloroform
  7. customThe chloroform was removed

出典と根拠

ORDレコード
ord-c4f3acd7d7e94ed39bc67ad173bb9014
出典データセット
uspto-grants-2014_09
特許番号
US08846937B2

関連ノート

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