4-Bromobenzyl bromide → 3-{3-[3-(4-Bromo-benzyl)-2-imino-2,3-dihydro-benzoimidazol-1-yl]-propoxy}-benzoic acid ethyl ester, hydrobromide salt

HRID 410362Notes

Reaction equation

HRID 410362 reaction equation
[CH2:1]([O:3][C:4](=[O:25])[C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([O:11][CH2:12][CH2:13][CH2:14][N:15]2[C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=3[NH:17][C:16]2=[NH:24])[CH:6]=1)[CH3:2].[Br:26][C:27]1[CH:34]=[CH:33][C:30]([CH2:31]Br)=[CH:29][CH:28]=1>CC(=O)CC>[BrH:26].[CH2:1]([O:3][C:4](=[O:25])[C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([O:11][CH2:12][CH2:13][CH2:14][N:15]2[C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=3[N:17]([CH2:31][C:30]3[CH:33]=[CH:34][C:27]([Br:26])=[CH:28][CH:29]=3)[C:16]2=[NH:24])[CH:6]=1)[CH3:2]

Participants

4

Reactant 2

HCID 685274-Bromobenzyl bromideHCID 178468935HCID 178468935, compound

Product 1

HCID 1317316403-{3-[3-(4-Bromo-benzyl)-2-imino-2,3-dihydro-benzoimidazol-1-yl]-propoxy}-benzoic acid ethyl ester, hydrobromide saltYield 72.5%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 3-[3-(2-imino-2,3-dihydro-benzoimidazol-1-yl)-propoxy]-benzoic acid ethyl ester (2.45 g, 7.3 mmol) in 2-butanone (125 ml) was added 4-bromobenzylbromide (2.88 g, 11.7 mmol). The reaction was heated to 80° C. where it was maintained for 24 h. After this time the mixture was cooled to rt and filtered. The collected solids were washed with additional cold 2-butanone and then dried to give 3-{3-[3-(4-bromo-benzyl)-2-imino-2,3-dihydro-benzoimidazol-1-yl]-propoxy}-benzoic acid ethyl ester, hydrobromide salt (2.5 g, 59%). HPLC-MS 508, 510 [M+1]+.

Workup

  1. temperaturewas maintained for 24 h
  2. temperatureAfter this time the mixture was cooled to rt
  3. filtrationfiltered
  4. washThe collected solids were washed with additional cold 2-butanone
  5. customdried

Sources & evidence

ORD record
ord-8c403b880bb1440ab3ba0b356cdcd7a9
Source dataset
uspto-grants-2014_06
Patent number
US08759520B2

Reaction notes

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