2-(7-bromo-1H-benzimidazol-1-yl)ethanol → 1-(2-Hydroxyethyl)-1H-benzimidazole-7-carbonitrile

HRID 1991203Notes

Reaction equation

HRID 1991203 reaction equation
[OH:1][CH2:2][CH2:3][NH:4][C:5]1[C:12]([N+:13]([O-])=O)=[CH:11][CH:10]=[CH:9][C:6]=1[C:7]#[N:8].Br[C:17]1C2N(CCO)C=NC=2C=CC=1>>[OH:1][CH2:2][CH2:3][N:4]1[C:5]2[C:6]([C:7]#[N:8])=[CH:9][CH:10]=[CH:11][C:12]=2[N:13]=[CH:17]1

Participants

3

Reactant 2

HCID 113454912-(7-bromo-1H-benzimidazol-1-yl)ethanolHCID 114470952-[(2-Hydroxyethyl)amino]-3-nitrobenzonitrile

Product 1

HCID 114467811-(2-Hydroxyethyl)-1H-benzimidazole-7-carbonitrile

Procedure

1-(2-Hydroxyethyl)-1H-benzimidazole-7-carbonitrile was prepared in two steps starting from 2-[(2-hydroxyethyl)amino]-3-nitrobenzonitrile (0.99 g) according to the procedure described for the synthesis of 2-(7-bromo-1H-benzimidazol-1-yl)ethanol. Yield 0.49 g (55 %). MS (ESI) m/z 188.1 [M+H]. 1H NMR (400 MHz, DMSO-D6) δ ppm: 3.81 (q, J=5.1 Hz, 2H), 4.53 (t, J=5.3 Hz, 2H), 5.03 (t, J=5.1 Hz, 1H) 7.36 (t, J=7.8 Hz, 1H), 7.76 (dd, J=7.6, 1.0 Hz, 1H), 8.04 (dd, J=8.1, 1.0 Hz, 1H), 8.37 (s, 1H).

Sources & evidence

ORD record
ord-0b564a011b34485b9bc975d3c3939f78
Source dataset
uspto-grants-2010_01
Patent number
US07645784B2

Reaction notes

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