Acetic Anhydride → 5-(5-Acetylaminobenzoxazol-2-yl)-2-methyl-1-n-propylbenzimidazole

HRID 74281Notes

Reaction equation

HRID 74281 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([C:10]3[CH:22]=[CH:21][C:13]4[N:14]([CH2:18][CH2:19][CH3:20])[C:15]([CH3:17])=[N:16][C:12]=4[CH:11]=3)=[N:7][C:6]=2[CH:23]=1.C(N(CC)CC)C.[C:31](OC(=O)C)(=[O:33])[CH3:32]>C(Cl)(Cl)Cl>[C:31]([NH:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([C:10]3[CH:22]=[CH:21][C:13]4[N:14]([CH2:18][CH2:19][CH3:20])[C:15]([CH3:17])=[N:16][C:12]=4[CH:11]=3)=[N:7][C:6]=2[CH:23]=1)(=[O:33])[CH3:32]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 67498866HCID 67498866, compound

Product 1

HCID 674976975-(5-Acetylaminobenzoxazol-2-yl)-2-methyl-1-n-propylbenzimidazoleYield 77.4%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 5-(5-aminobenzoxazol-2-yl)-2-methyl-1-n-propylbenzimidazole (see Working Example 82-4) (200 mg, 0.653 mmol) in chloroform (5 mL) was added triethylamine (132 mg, 1.31 mmol) and acetic anhydride (100 mg, 0.979 mmol), and this was stirred at room temperature for 20 hours. After the reaction was complete, the solution was concentrated, the precipitated crystals were filtered, and after washing with water were dried to yield the title compound (176 mg, 77% yield) as pale yellow crystals.

Workup

  1. concentrationthe solution was concentrated
  2. filtrationthe precipitated crystals were filtered
  3. washafter washing with water
  4. customwere dried

Sources & evidence

ORD record
ord-2002831dc48e4fa782897298ccbf5a57
Source dataset
uspto-grants-2014_09
Patent number
US08829035B2

Reaction notes

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