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O-Phenylenediamine → N,N-bis(1H-benzimidazol-2-ylmethyl)-N-benzylamine

HRID 1765960
ノート
印刷プレビュー

反応式

HRID 1765960 の反応式
[CH2:1]([N:8]([CH2:13][C:14](O)=O)[CH2:9][C:10](O)=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:17]1([NH2:24])[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[NH2:23]>C(O)CO.O>[NH:23]1[C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=2[N:24]=[C:10]1[CH2:9][N:8]([CH2:13][C:14]1[NH:24][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[N:23]=1)[CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 2

HCID 7243O-PhenylenediamineHCID 77606N-Benzylaminodiacetic acid

生成物 1

HCID 21107922N,N-bis(1H-benzimidazol-2-ylmethyl)-N-benzylamine

試薬・触媒・溶媒 2

HCID 174Ethylene Glycol溶媒HCID 962Water溶媒2 回

反応条件

温度
190 °C

実験手順

A mixture of 4.00 g (17.9 mmol) N-benzyliminodiacetic acid and 3.86 g (35.8 mmol) o-phenylene diamine in 30 ml ethylene glycol was stirred at 190° C. for 4 hours. The water produced during was distilled off continuously. At the end of the reaction, the reaction mixture was allowed to cool down to room temperature and then poured in 150 ml water. The obtained slurry was triturated for 30 min, filtered, washed with water (3×30 ml) and dried at 60° C. under reduced pressure for 48 hours. Yield 4.94 g (75.0%). 1H NMR (250 MHz, DMSO-d6), δ 3.72 (s, 2H), 3.92 (s, 4H), 7.13–7.57 (m, 13H), 12.37 (Br. s, 2H). +CI MS (m/z): [368]. (+CI-MS is Positive Chemical Ionisation Mass Spectroscopy).

後処理

  1. distillationduring was distilled off continuously
  2. customAt the end of the reaction
  3. temperatureto cool down to room temperature
  4. customThe obtained slurry was triturated for 30 min
  5. filtrationfiltered
  6. washwashed with water (3×30 ml)
  7. customdried at 60° C. under reduced pressure for 48 hours

出典と根拠

ORDレコード
ord-9a27c2fa1bbd4698a244ede6b83623a9
出典データセット
uspto-grants-2007_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07229943B2

反応ノート

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