Sodium Hydroxide → HCID 67429089, compound

HRID 410374Notes

Reaction equation

HRID 410374 reaction equation
C[O:2][C:3](=[O:32])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([O:10][CH2:11][CH2:12][CH2:13][N:14]2[C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=3[N:16]([CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[C:26]([Br:30])[CH:25]=3)[C:15]2=[NH:31])[CH:5]=1.[OH-].[Na+:34]>CCO>[Na+:34].[Br:30][C:26]1[CH:25]=[C:24]([CH:29]=[CH:28][CH:27]=1)[CH2:23][N:16]1[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[N:14]([CH2:13][CH2:12][CH2:11][O:10][C:6]2[CH:5]=[C:4]([CH:9]=[CH:8][CH:7]=2)[C:3]([O-:32])=[O:2])[C:15]1=[NH:31]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 58564947HCID 58564947, compound

Product 1

HCID 67429089HCID 67429089, compoundYield 85.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 3-{3-[3-(3-bromo-benzyl)-2-imino-2,3-dihydro-benzoimidazol-1-yl]-propoxy}-benzoic acid methyl ester (0.50 g, 0.98 mmol) in EtOH (10 ml) at rt is added NaOH (71 mg, 1.77 mmol). The reaction was stirred until the complete consumption of starting material was observed by TLC. After this time, the mixture was concentrated under reduced pressure and then the material that remained was suspended in EtOAc and H2O. The suspension was filtered and the collected solid was dried to provide 3-{3-[3-(3-bromo-benzyl)-2-imino-2,3-dihydro-benzoimidazol-1-yl]-propoxy}-benzoic acid sodium salt (0.42 g, 85%). HPLC-MS 480, 482 [M+1]+.

Workup

  1. concentrationAfter this time, the mixture was concentrated under reduced pressure
  2. filtrationThe suspension was filtered
  3. customthe collected solid was dried

Sources & evidence

ORD record
ord-090899af46fa4e399eaaa55c9ca7ecc8
Source dataset
uspto-grants-2014_06
Patent number
US08759520B2

Reaction notes

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