Ethyl orthoformate → (6-Bromo-1-methyl-1H-benzoimidazol-4-yl)-bis-(4-methoxy-benzyl)-amine

HRID 59935Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[C:4]([NH:28][CH3:29])[C:5]([NH2:27])=[C:6]([N:8]([CH2:18][C:19]2[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=2)[CH2:9][C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=2)[CH:7]=1.[CH:30](OCC)(OCC)OCC>CC#N>[Br:1][C:2]1[CH:7]=[C:6]([N:8]([CH2:18][C:19]2[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=2)[CH2:9][C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=2)[C:5]2[N:27]=[CH:29][N:28]([CH3:30])[C:4]=2[CH:3]=1

Participants

Conditions

Temperature: 85 °C

Procedure

5-Bromo-N,N-bis-(4-methoxy-benzyl)-N″-methyl-benzene-1,2,3-triamine (170 mmol) was dissolved in a mixture of HC(OEt)3 (100 mol) and MeCN (500 mL). The mixture was stirred at 85° C. for 0.5 h and then at room temperature for approximately 16 h. The mixture was combined with another one obtained following the same procedure described above. The resulting mixture was concentrated and the residue was purified by flash column chromatography (SiO2, 15:85 to 60:40 EtOAc/petroleum ether) to obtain the desired product.

Workup

waitat room temperature for approximately 16 h
customobtained
concentrationThe resulting mixture was concentrated
customthe residue was purified by flash column chromatography (SiO2, 15:85 to 60:40 EtOAc/petroleum ether)

Sources & evidence

ORD record: ord-1bc05a61a54f45e8bfa4316fb3c7d9b9
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09440929B2

Reaction notes

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