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

HRID 1765960Notes

Reaction equation

[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

Participants

Conditions

Temperature: 190 °C

Procedure

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).

Workup

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

Sources & evidence

ORD record: ord-9a27c2fa1bbd4698a244ede6b83623a9
Source dataset: uspto-grants-2007_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07229943B2

Reaction notes

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