3H-Indole, 2,3,3-trimethyl- → 2,3,3-trimethyl-1-(3-triethylammoniopropyl)-3H-indolium bromide chloride

HRID 403608

反応式

HRID 403608 の反応式
[CH3:1][C:2]1[C:10]([CH3:12])([CH3:11])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.[Cl-:13].[Br:14][CH2:15][CH2:16][CH2:17][N+:18]([CH2:23][CH3:24])([CH2:21][CH3:22])[CH2:19][CH3:20]>>[Cl-:13].[Br-:14].[CH3:1][C:2]1[C:10]([CH3:12])([CH3:11])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N+:3]=1[CH2:15][CH2:16][CH2:17][N+:18]([CH2:23][CH3:24])([CH2:21][CH3:22])[CH2:19][CH3:20]

参加物

3

反応物 2

HCID 154273H-Indole, 2,3,3-trimethyl-HCID 89781116N-(3-bromopropyl)triethylammonium chloride

生成物 1

HCID 897815802,3,3-trimethyl-1-(3-triethylammoniopropyl)-3H-indolium bromide chloride収率 36%

反応条件

温度
140 °C

実験手順

Freshly distilled 2,3,3-trimethylindolenine (0.53 g, 3.3 mmol) and N-(3-bromopropyl)triethylammonium chloride (1.01 g, 3.9 mmol) were mixed in the thick-wall tube and placed under an argon atmosphere. The mixture was then heated at 140° C. for 1.5 h, giving a deep red viscous product, which solidified to a glass on cooling. It was ground to a powder under acetone; product was collected by filtration, triturated 3 times with 10 mL portions of acetone and dried under vacuum to give 0.45 g (36%) of 2,3,3-trimethyl-1-(3-triethylammoniopropyl)-3H-indolium bromide chloride as a white powder. δH (200 MHz, DMSO-d6) 8.10 (1H, d, 6.7 Hz, arom.), 7.87 (1H, d, 5.8 Hz, arom.), 7.75-7.58 (2H, m, arom.), 4.56 (2H, t, 7.3 Hz, N+CH2), 3.27 (6H, q, 6.0 Hz, N+(CH2)3), 2.91 (3H, s, CH3), 2.34-2.10 (2H, m, N+CH2), 1.56 (6H, s, (CH3)2) 1.36-1.05 (11H, m, CH2, (CH3)3).

後処理

  1. customgiving a deep red viscous product, which
  2. temperatureon cooling
  3. filtrationproduct was collected by filtration
  4. customtriturated 3 times with 10 mL portions of acetone
  5. customdried under vacuum

出典と根拠

ORDレコード
ord-42be14ad864246099ad5c240b809973e
出典データセット
uspto-grants-2014_06
特許番号
US08748446B2

関連ノート

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