4-(Bromomethyl)benzaldehyde → 4-{3-[3-(4-Fluoro-phenoxy)-propyl]-2-imino-2,3-dihydro-benzoimidazol-1-ylmethyl}-benzaldehyde hydrobromide salt

HRID 410348Notes

Reaction equation

HRID 410348 reaction equation
[F:1][C:2]1[CH:21]=[CH:20][C:5]([O:6][CH2:7][CH2:8][CH2:9][N:10]2[C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=3[NH:12][C:11]2=[NH:19])=[CH:4][CH:3]=1.[Br:22][CH2:23][C:24]1[CH:31]=[CH:30][C:27]([CH:28]=[O:29])=[CH:26][CH:25]=1>CC(=O)CC>[BrH:22].[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:6][CH2:7][CH2:8][CH2:9][N:10]2[C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=3[N:12]([CH2:23][C:24]3[CH:31]=[CH:30][C:27]([CH:28]=[O:29])=[CH:26][CH:25]=3)[C:11]2=[NH:19])=[CH:20][CH:21]=1

Participants

4

Reactant 2

HCID 112064214-(Bromomethyl)benzaldehydeHCID 178509078HCID 178509078, compound

Product 1

HCID 867624844-{3-[3-(4-Fluoro-phenoxy)-propyl]-2-imino-2,3-dihydro-benzoimidazol-1-ylmethyl}-benzaldehyde hydrobromide saltYield 49.2%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

To a solution of 1-[3-(4-fluoro-phenoxy)-propyl]-1,3-dihydro-benzoimidazol-2-ylideneamine (0.96 g, 3.36 mmol) in 2-butanone (50 ml) was added 4-bromomethyl benzaldehyde (1.0 g, 5.03 mmol). The reaction was heated to reflux where it was maintained for 48 h. After this time, the suspension was cooled to rt and filtered. The collected solid was washed with additional 2-butanone and then dried to provide 4-{3-[3-(4-fluoro-phenoxy)-propyl]-2-imino-2,3-dihydro-benzoimidazol-1-ylmethyl}-benzaldehyde hydrobromide salt (0.80 g, 49%) as a yellow solid which was used without further purification. HPLC-MS 404 [M+1]+.

Workup

  1. temperatureThe reaction was heated
  2. temperatureto reflux where it
  3. temperaturewas maintained for 48 h
  4. filtrationfiltered
  5. washThe collected solid was washed with additional 2-butanone
  6. customdried

Sources & evidence

ORD record
ord-ce68a789c01c4acb82f8514bddd44905
Source dataset
uspto-grants-2014_06
Patent number
US08759520B2

Reaction notes

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