2,6-Dimethylaniline → HCID 178424805、化合物

HRID 925015

反応式

HRID 925015 の反応式
[CH3:1][C:2]1[CH:8]=[CH:7][CH:6]=[C:5]([CH3:9])[C:3]=1[NH2:4].C([Li])CCC.[C:15]([C:19]1[CH:26]=[CH:25][C:22]([C:23]#[N:24])=[CH:21][CH:20]=1)([CH3:18])([CH3:17])[CH3:16]>O>[C:15]([C:19]1[CH:20]=[CH:21][C:22]([C:23]([NH:4][C:3]2[C:5]([CH3:9])=[CH:6][CH:7]=[CH:8][C:2]=2[CH3:1])=[NH:24])=[CH:25][CH:26]=1)([CH3:18])([CH3:16])[CH3:17]

参加物

5

反応物 3

HCID 68962,6-DimethylanilineHCID 778834-tert-ButylbenzonitrileHCID 178418339Butyllithium

生成物 1

HCID 178424805HCID 178424805、化合物収率 79.8%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

Procedure as described for Amidine I using the following amounts: 6.15 mL of 2,6-dimethylaniline (50.0 mmol); 26.0 mL of 2.0 M butyllithium (52.0 mmol), 8.50 mL of 4-t-butylbenzonitrile (50.0 mmol). After refluxing overnight, the solution was red-orange. Addition of water yielded a yellow solution with suspended solid. Solution was filtered, taken to dryness, resuspended in 100 mL of pentane and stirred vigorously for 1 hour. The resulting white solid was filtered and dried in vacuo yielding 11.19 g of white powder. The filtrate was concentrated to approximately 50 mL and cooled to −10° C. An additional 1.47 g of solid was isolated. Total yield 10.60 g (76%). 1H NMR (400 MHz, CDCl3): 7.87 (d, 2H), 7.50 (d, 2H), 7.04 (d, 2H), 6.90 (t, 1H), 4.56 (s, 2H), 2.15 (s, 6H), 1.36 (s, 9H). 13C {1H} NMR (100 MHz, CDCl3): 154.27, 153.01, 146.97, 133.12, 129.16, 128.53, 126.83, 125.88, 123.05, 35.21, 31.59, 18.17.

後処理

  1. temperatureAfter refluxing overnight
  2. customyielded a yellow solution
  3. filtrationSolution was filtered
  4. filtrationThe resulting white solid was filtered
  5. customdried in vacuo

出典と根拠

ORDレコード
ord-6abc2fb3476d44248e4b645d53336da4
出典データセット
uspto-grants-2016_03
特許番号
US09283555B2

関連ノート

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