Acetaldehyde → 5-(Benzoxazol-2-yl)-2-methyl-1-tert-butylbenzimidazole

HRID 74197Notes

Reaction equation

HRID 74197 reaction equation
[C:1]([NH:5][C:6]1[CH:12]=[CH:11][C:10]([C:13]2[O:14][C:15]3[CH:21]=[CH:20][CH:19]=[CH:18][C:16]=3[N:17]=2)=[CH:9][C:7]=1[NH2:8])([CH3:4])([CH3:3])[CH3:2].[CH:22](=O)[CH3:23].OOS([O-])=O.[K+].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[O:14]1[C:15]2[CH:21]=[CH:20][CH:19]=[CH:18][C:16]=2[N:17]=[C:13]1[C:10]1[CH:11]=[CH:12][C:6]2[N:5]([C:1]([CH3:4])([CH3:2])[CH3:3])[C:22]([CH3:23])=[N:8][C:7]=2[CH:9]=1

Participants

6

Reactant 4

HCID 177AcetaldehydeHCID 11430Potassium CarbonateHCID 23707502Potassium hydroxy sulfiteHCID 674984142-(2-Tert-butylaminoanilin-5-yl)benzoxazole

Product 1

HCID 674979235-(Benzoxazol-2-yl)-2-methyl-1-tert-butylbenzimidazoleYield 38%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-(2-tert-butylaminoanilin-5-yl)benzoxazole (see Working Example 29-1) (45.0 mg, 0.160 mmol) in dimethylformamide (2 mL) was added an aqueous solution of acetaldehyde (approx. 90%, 235 μL, 0.480 mmol) and oxone (63.9 mg, 0.104 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-2c534f3886654c50aba4cc10635778be
Source dataset
uspto-grants-2014_09
Patent number
US08829035B2

Reaction notes

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