Water → N-(2-(4-Chlorobenzylthio)benzo[d]oxazol-5-yl)acetamide

HRID 1886934Notes

Reaction equation

HRID 1886934 reaction equation
[Cl:1][C:2]1[CH:19]=[CH:18][C:5]([CH2:6][S:7][C:8]2[O:9][C:10]3[CH:16]=[CH:15][C:14]([NH2:17])=[CH:13][C:11]=3[N:12]=2)=[CH:4][CH:3]=1.[C:20](Cl)(=[O:22])[CH3:21].O>N1C=CC=CC=1>[Cl:1][C:2]1[CH:19]=[CH:18][C:5]([CH2:6][S:7][C:8]2[O:9][C:10]3[CH:16]=[CH:15][C:14]([NH:17][C:20](=[O:22])[CH3:21])=[CH:13][C:11]=3[N:12]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 6367Acetyl chlorideHCID 613592742-(4-Chlorobenzylthio)benzo[d]oxazol-5-amine

Product 1

HCID 67331899N-(2-(4-Chlorobenzylthio)benzo[d]oxazol-5-yl)acetamideYield 40.1%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 2-(4-chlorobenzylthio)benzo[d]oxazol-5-amine (87 mg, 0.30 mmol) in dry pyridine (3 mL) at room temperature was added acetyl chloride (21 μL, 0.30 mmol). The resulting solution was stirred at room temperature for 16 h. Water was then added, the precipitate was collected by filtration, washed with diluted aqueous hydrochloric acid and then with water. Trituration with diethyl ether afforded 40 mg (40%) of the title compound (LCMS RT=6.40 min, MH+ 333.1)

Workup

  1. filtrationthe precipitate was collected by filtration
  2. washwashed with diluted aqueous hydrochloric acid

Sources & evidence

ORD record
ord-10dd84aed8514efc94bd121618278f45
Source dataset
uspto-grants-2013_08
Patent number
US08501713B2

Reaction notes

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