Acetic Anhydride → HCID 21846996, compound

HRID 619741Notes

Reaction equation

HRID 619741 reaction equation
[C:1]([O:4][C:5](=O)[CH3:6])(=O)[CH3:2].[NH2:8][C:9]1C=C[C:12]([S:15][C:16]2[CH:25]=[CH:24][CH:23]=[C:22]3[C:17]=2[CH:18]=[CH:19][N:20]=[CH:21]3)=[CH:11][C:10]=1O>C(OCC)(=O)C>[CH:21]1[C:22]2[C:17](=[C:16]([S:15][C:12]3[CH:11]=[CH:10][C:9]4[N:8]=[C:5]([CH3:6])[O:4][C:1]=4[CH:2]=3)[CH:25]=[CH:24][CH:23]=2)[CH:18]=[CH:19][N:20]=1

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 21846956HCID 21846956, compound

Product 1

HCID 21846996HCID 21846996, compoundYield 50.6%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
200 °C

Procedure

Acetic anhydride 0.6 ml was added to 2-amino-5-(5-isoquinolylsulfanyl)phenol 210 mg (0.8 mmol), and the mixture was heated for 1 hour at 200° C. Ethyl acetate was added to the reaction solution, and the organic layer was washed with 0.5 N sodium hydroxide, water and saturated sodium chloride. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (NH-silica gel, hexane:ethyl acetate=1:1), and 6-(5-isoquinolylsulfanyl)-2-methylbenzo[d][1,3]oxazole 120 mg (50.6%) was obtained.

Workup

  1. washthe organic layer was washed with 0.5 N sodium hydroxide, water and saturated sodium chloride
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customthe resulting residue was purified by silica gel column chromatography (NH-silica gel, hexane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-487a05315967453693e0ae96ee4f80f9
Source dataset
uspto-grants-1999_09
Patent number
US05959107

Reaction notes

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