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Acetaldehyde → 5-(Benzoxazol-2-yl)-1-(2-methoxyphenyl)-2-methylbenzimidazole

HRID 74199
Notes
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Reaction equation

HRID 74199 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[NH:9][C:10]1[CH:16]=[CH:15][C:14]([C:17]2[O:18][C:19]3[CH:25]=[CH:24][CH:23]=[CH:22][C:20]=3[N:21]=2)=[CH:13][C:11]=1[NH2:12].[CH:26](=O)[CH3:27].OOS([O-])=O.[K+].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[O:18]1[C:19]2[CH:25]=[CH:24][CH:23]=[CH:22][C:20]=2[N:21]=[C:17]1[C:14]1[CH:15]=[CH:16][C:10]2[N:9]([C:4]3[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=3[O:2][CH3:1])[C:26]([CH3:27])=[N:12][C:11]=2[CH:13]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 177AcetaldehydeHCID 11430Potassium CarbonateHCID 23707502Potassium hydroxy sulfiteHCID 674989942-(2-(2-Methoxyphenyl)aminoanilin-5-yl)benzoxazole

Product 1

HCID 674978465-(Benzoxazol-2-yl)-1-(2-methoxyphenyl)-2-methylbenzimidazoleYield 38%

Reagents, catalysts & solvents 1

HCID 6228
Dimethylformamide
Solvent

Procedure

To a solution of 2-(2-(2-methoxyphenyl)aminoanilin-5-yl)benzoxazole (see Working Example 30-1) (48.0 mg, 0.135 mmol) in dimethylformamide (2 mL) was added an aqueous solution of acetaldehyde (approx. 90%, 20.5 μL, 0.405 mmol) and oxone (53.9 mg, 0.0878 mmol), and this was stirred at room temperature for 3 hours. After the reaction was complete, aqueous potassium carbonate solution was added, this was filtered and washed with water. The crystals obtained were purified by silica gel column chromatography to yield the title compound (18.2 mg, 38% yield) as white crystals.

Workup

  1. filtrationthis was filtered
  2. washwashed with water
  3. customThe crystals obtained
  4. customwere purified by silica gel column chromatography

Sources & evidence

ORD record
ord-3017393069a2499c84c58ae46a6c581f
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