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Methanol → HCID 67499138, compound

HRID 74303
Notes
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Reaction equation

HRID 74303 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]1[CH:30]=[CH:29][C:13]2[N:14]([CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([C:25]([O:27]C)=[O:26])[CH:20]=3)[C:15]([CH3:17])=[N:16][C:12]=2[CH:11]=1.[OH-].[Na+].CO>C(Cl)(Cl)Cl>[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]1[CH:30]=[CH:29][C:13]2[N:14]([CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([C:25]([OH:27])=[O:26])[CH:20]=3)[C:15]([CH3:17])=[N:16][C:12]=2[CH:11]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 674984625-(Benzoxazol-2-yl)-1-(3-methoxycarbonylphenylmethyl)-2-methylbenzimidazole

Product 1

HCID 67499138HCID 67499138, compoundYield 99.4%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 5-(benzoxazol-2-yl)-1-(3-methoxycarbonylphenylmethyl)-2-methylbenzimidazole (see Working Example 117-2) (125 mg, 0.315 mmol) in chloroform (3 mL) was added aqueous sodium hydroxide solution (1 M, 1 mL, 1 mmol). This two-layer solution was homogenized by the addition of methanol, and this was stirred at room temperature for 20 hours. After the reaction was complete, the solution was concentrated, aqueous acetic acid solution was added, and this was stirred at room temperature. The precipitated crystals were filtered, and after washing with water were dried to yield the title compound (120 mg, 99% yield) as white crystals.

Workup

  1. concentrationthe solution was concentrated
  2. additionaqueous acetic acid solution was added
  3. stirringthis was stirred at room temperature
  4. filtrationThe precipitated crystals were filtered
  5. washafter washing with water
  6. customwere dried

Sources & evidence

ORD record
ord-81e80b406c8b43288fdbb6c0ce9fd441
Source dataset
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08829035B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes