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

HRID 1765959Notes

Reaction equation

[CH3:1][N:2]([CH2:7][C:8](O)=O)[CH2:3][C:4](O)=O.[C:11]1([NH2:18])[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[NH2:17]>C(O)CO.O>[NH:17]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[N:18]=[C:4]1[CH2:3][N:2]([CH2:7][C:8]1[NH:18][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[N:17]=1)[CH3:1]

Participants

Conditions

Temperature: 190 °C

Procedure

A mixture of 4.00 g (27.2 mmol) N-methyliminodiacetic acid and 5.99 g (54.4 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 6.88 g (87.0%). 1H NMR (250 MHz, DMSO-d6), δ 2.25 (s, 3H), 3.90 (s, 4H), 7.15 (m, 4H), 7.47–4.58 (m, 4H), 12.33 (br. s, 2E). Microanalysis, %: Calculated for C17H17N5: C, 70.10; H, 5.84; N, 24.05. Found: C, 70.22; H, 6.05; N, 23.76. +CI MS (m/z): [292]. (+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-114e21e4575440c2aae46bcac84b602a
Source dataset: uspto-grants-2007_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07229943B2

Reaction notes

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