HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

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

HRID 1765960
Notes
Print preview

Reaction equation

HRID 1765960 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 7243O-PhenylenediamineHCID 77606N-Benzylaminodiacetic acid

Product 1

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

Reagents, catalysts & solvents 2

HCID 174Ethylene GlycolSolventHCID 962WaterSolvent2×

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

  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

Sources & evidence

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

Reaction notes

Loading…

On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes