1,2-Ethanediamine, N1-phenyl- → HCID 67030483, compound

HRID 1685127Notes

Reaction equation

Cl[C:2]1[NH:6][C:5]2[CH:7]=[CH:8][C:9]([Cl:11])=[CH:10][C:4]=2[N:3]=1.[C:12]1([NH:18][CH2:19][CH2:20][NH2:21])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(N(CC)C(C)C)(C)C>>[Cl:11][C:9]1[CH:8]=[CH:7][C:5]2[N:6]=[C:2]([NH:21][CH2:20][CH2:19][NH:18][C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[NH:3][C:4]=2[CH:10]=1

Participants

Reactant 3

HCID 742701,2-Ethanediamine, N1-phenyl-

HCID 81531Diisopropylethylamine

HCID 3354732,5-Dichlorobenzimidazole

Product 1

HCID 67030483HCID 67030483, compoundYield 62.6%

Conditions

Temperature: 110 °C

Procedure

A neat mixture of 2,5-dichloro-1H-benzoimidazole (150 mg, 0602 mmol), N-phenyl ethylenediamine (110 mg, 0.808 mmol, 1 eq) and N,N-diisopropylethyl amine (210 mL, 1.21 mmol, 1.5 eq.) in sealed tube was heated overnight at 110° C. The mixture was directly loaded onto a silica gel column and eluted with 5% methanol in dichloromethane to provide 144 mg of N1-(6-chloro-1H-benzo[d]imidazol-2-yl)-N2-phenylethane-1,2-diamine.

Workup

washeluted with 5% methanol in dichloromethane

Sources & evidence

ORD record: ord-166c8ec879184cb5ba40dddebf9f8ffe
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08148363B2

Reaction notes

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