Water → N-[4-(5-chloro-1,3-benzoxazol-2-yl)phenyl]acetamide

HRID 1896759Notes

Reaction equation

HRID 1896759 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([C:10]3[CH:16]=[CH:15][C:13]([NH2:14])=[CH:12][CH:11]=3)=[N:7][C:6]=2[CH:17]=1.[C:18](Cl)(=[O:20])[CH3:19].O>N1C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([C:10]3[CH:16]=[CH:15][C:13]([NH:14][C:18](=[O:20])[CH3:19])=[CH:12][CH:11]=3)=[N:7][C:6]=2[CH:17]=1

Participants

5

Reactant 3

HCID 962WaterHCID 6367Acetyl chlorideHCID 7210584-(5-Chloro-1,3-benzoxazol-2-YL)phenylamine

Product 1

HCID 401582N-[4-(5-chloro-1,3-benzoxazol-2-yl)phenyl]acetamideYield 84%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 4-(5-chlorobenzo[d]oxazol-2-yl)aniline (122.3 mg, 0.50 mmol) in pyridine (3 mL) at room temperature was added acetyl chloride (39 μL, 0.55 mmol). The resulting mixture was stirred at room temperature for 16 h. The solution was then poured into water, and the resulting precipitate collected by filtration. The solid was washed with diluted hydrochloric acid solution, followed by diluted sodium hydroxide solution, and then by water to afford 120 mg (84%) of the title compound (LCMS RT=6.38 min, MH+ 287.0)

Workup

  1. filtrationthe resulting precipitate collected by filtration
  2. washThe solid was washed with diluted hydrochloric acid solution

Sources & evidence

ORD record
ord-1f6f480266274f30a228d6ab674cb03b
Source dataset
uspto-grants-2013_08
Patent number
US08518980B2

Reaction notes

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