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

HRID 1765960
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HRID 1765960 반응식
[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
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 2

HCID 7243O-PhenylenediamineHCID 77606N-Benzylaminodiacetic acid

생성물 1

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

시약·촉매·용매 2

HCID 174Ethylene Glycol용매HCID 962Water용매2회

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온도
190 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-9a27c2fa1bbd4698a244ede6b83623a9
출처 데이터셋
uspto-grants-2007_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07229943B2

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