Water → HCID 178419696, compound

HRID 415055Notes

Reaction equation

HRID 415055 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([CH2:7][O:8][C:9]2[CH:10]=[C:11]([NH2:16])[C:12]([NH2:15])=[CH:13][CH:14]=2)=[CH:3][CH:2]=1.O.[N:18]#[C:19][Br:20]>C(#N)C>[BrH:20].[N:1]1[CH:6]=[CH:5][C:4]([CH2:7][O:8][C:9]2[CH:14]=[CH:13][C:12]3[NH:15][C:19]([NH2:18])=[N:16][C:11]=3[CH:10]=2)=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 962WaterHCID 10476Cyanogen BromideHCID 59349546HCID 59349546, compound

Product 1

HCID 178419696HCID 178419696, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

4-(Pyridin-4-ylmethoxy)benzene-1,2-diamine (21.4 mmoles, 0.460 g, 1 equivalent) was dissolved in acetonitrile (10 ml) and water (5 ml) and cooled to 0-5° C. (ice-water). Cyanogen bromide (0.226 g, 21.4 mmoles, 1 equivalent) was added in one lot and the reaction mixture was allowed to go to room temperature and stirred for 16 hours. The reaction mixture was then evaporated under reduced pressure to 0.4571 g of 5-(pyridin-4-ylmethoxy)-1H-benzo[d]imidazol-2-amine hydrobromide (yield: 86%) which was used directly in the next reaction without any further reaction. 1H-NMR (400 MHz, DMSO-d6) 12.60 (br s, 1H), 8.56 (s, 2H), 7.58 (m, 1H), 8.23 (br s, 3h), 7.57 (m, 1H), 7.40 (m, 1H), 5.28 (s, 2H). (MS (EI): 241 (MH+).

Workup

  1. customto go to room temperature

Sources & evidence

ORD record
ord-0db057cbd7c3436a88d56757d151f565
Source dataset
uspto-grants-2012_01
Patent number
US08088767B2

Reaction notes

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