Ethyl Acetate → 2-(4-Chlorobenzylthio)benzo[d]oxazol-5-amine

HRID 1896765Notes

Reaction equation

HRID 1896765 reaction equation
[Cl:1][C:2]1[CH:21]=[CH:20][C:5]([CH2:6][S:7][C:8]2[O:9][C:10]3[CH:16]=[CH:15][C:14]([N+:17]([O-])=O)=[CH:13][C:11]=3[N:12]=2)=[CH:4][CH:3]=1.[Cl-].[NH4+].C(OCC)(=O)C>C(O)C.O.[Fe]>[Cl:1][C:2]1[CH:21]=[CH:20][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

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 25517Ammonium ChlorideHCID 673325842-(4-Chlorobenzylthio)-5-nitrobenzo[d]oxazole

Product 1

HCID 613592742-(4-Chlorobenzylthio)benzo[d]oxazol-5-amineYield 94%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 19096565Water ethanolSolvent

Conditions

Temperature
90 °C

Procedure

To a suspension of 2-(4-chlorobenzylthio)-5-nitrobenzo[d]oxazole (220 mg, 0.70 mmol) in ethanol/water (5 mL/5 mL) at 90° C. was added ammonium chloride (75 mg, 1.4 mmol), followed by iron powder (192 mg, 3.44 mmol). The resulting mixture was stirred for 4 h at 90° C. After cooling, ethyl acetate was added and the solution was passed through a pad of Celite®. The organic layer was then washed with brine, dried over anhydrous MgSO4 and evaporated to afford 190 mg (94%) of the title compound (LCMS RT=6.54 min, MH+ 290.9)

Workup

  1. temperatureAfter cooling
  2. washThe organic layer was then washed with brine
  3. dry with materialdried over anhydrous MgSO4
  4. customevaporated

Sources & evidence

ORD record
ord-f1c078485baf41f3bbd74090b0a9c266
Source dataset
uspto-grants-2013_08
Patent number
US08518980B2

Reaction notes

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