Hydrochloric Acid → HCID 45256689, compound

HRID 1945284Notes

Reaction equation

HRID 1945284 reaction equation
[C:1]1([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH:6]=[CH:5][C:4]([C:7]2[C:27]([Cl:28])=[CH:26][C:10]3[NH:11][C:12]([O:14][C:15]4[CH:16]=[CH:17][C:18]([CH3:25])=[C:19]([CH:24]=4)[C:20]([O:22]C)=[O:21])=[N:13][C:9]=3[CH:8]=2)=[CH:3][CH:2]=1.[OH-].[Na+].Cl>CO.O.O>[C:1]1([C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=2)[CH:2]=[CH:3][C:4]([C:7]2[C:27]([Cl:28])=[CH:26][C:10]3[NH:11][C:12]([O:14][C:15]4[CH:16]=[CH:17][C:18]([CH3:25])=[C:19]([CH:24]=4)[C:20]([OH:22])=[O:21])=[N:13][C:9]=3[CH:8]=2)=[CH:5][CH:6]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 68488820HCID 68488820, compound

Product 1

HCID 45256689HCID 45256689, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 22242641Methanol--water (1/1)Solvent

Conditions

Temperature
70 °C

Procedure

To a solution of methyl 5-[(5-biphenyl-4-yl-6-chloro-1H-benzimidazol-2-yl)oxy]-2-methylbenzoate (11 g, 23.46 mmol) in MeOH/water (1:1) (250 mL) was added NaOH (5 M in water) (23.46 mL, 117 mmol). The mixture was heated at 70° C. for 1 h. The mixture was then cooled, diluted with water and acidified with 2 M aqueous HCl. The precipitated white solid was filtered and dried to afford the title compound as a white powder. LCMS: calculated for C27H19ClN2O3 454.90, observed m/e 455.5 (M+H)+ (Rt 2.27/4 min). 1H NMR (500 MHz, CD3OD): δ 7.98-7.35 (m, 14H), 2.62 (s, 3H).

Workup

  1. temperatureThe mixture was then cooled
  2. filtrationThe precipitated white solid was filtered
  3. customdried

Sources & evidence

ORD record
ord-ca42dde5bc554eee9cce60e9383eb543
Source dataset
uspto-grants-2013_03
Patent number
US08394969B2

Reaction notes

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