Triethylamine → Triethylammonium bromide

HRID 536221

反応式

HRID 536221 の反応式
[NH:1]1[CH2:5][CH2:4][N:3]=[C:2]1[C:6]1[CH:12]=[CH:11][CH:10]=[C:9]([O:13][CH3:14])[C:7]=1[NH2:8].[CH3:15][CH2:16][N:17]([CH2:20][CH3:21])[CH2:18][CH3:19].N#C[Br:24]>C(Cl)Cl>[CH3:14][O:13][C:9]1[C:7]2[N:8]=[C:16]([NH2:17])[N:3]3[CH2:4][CH2:5][N:1]=[C:2]3[C:6]=2[CH:12]=[CH:11][CH:10]=1.[N:17]([CH2:20][CH3:21])([CH2:18][CH3:19])[CH2:16][CH3:15].[BrH:24]

参加物

6

反応物 3

HCID 8471TriethylamineHCID 10476Cyanogen BromideHCID 583773572-(4,5-dihydro-1H-imidazol-2-yl)-6-methoxyaniline

生成物 2

HCID 2734074Triethylammonium bromide収率 296.1%HCID 178488375HCID 178488375、化合物

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
10 °C

実験手順

2-(4,5-Dihydro-1H-imidazol-2-yl)-6-methoxyaniline (Step 3, 22.0 g, 115 mmol) and Et3N (48.1 mL, 345 mmol) were dissolved in CH2Cl2 (200 mL), cooled to 10° C. in an ice bath and cyanogen bromide (24.4 g, 230 mmol) was added portionwise. A slight exotherm was noted, and the reaction was stirred overnight. The reaction was concentrated under reduced pressure, then treated with EtOAc (150 mL) and concentrated under reduced pressure again. Finally, the residue was treated with Heptane and concentrated under reduced pressure to give the title compound as a mixture with Et3N.HBr (62 g, 99%): HPLC MS RT=1.08 min, MH+=217.1; 1H NMR (DMSO-d6+2 drops TFA-d) δ: 3.85 (3H, s), 4.09-4.16 (2H, m), 4.31-4.38 (2H, m), 7.23 (1H, t), 7.31 (1H, d), 7.57 (1H, dd).

後処理

  1. concentrationThe reaction was concentrated under reduced pressure
  2. additiontreated with EtOAc (150 mL)
  3. concentrationconcentrated under reduced pressure again
  4. additionFinally, the residue was treated with Heptane
  5. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-cbf1799c49494e7eaaac2cf948a53bb4
出典データセット
uspto-grants-2014_10
特許番号
US08859572B2

関連ノート

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