Acetic Anhydride → HCID 19092704, compound

HRID 487703Notes

Reaction equation

HRID 487703 reaction equation
[C:1]([C:5]1[N:6]=[C:7]([C:10]2[O:11][C:12]3[CH:18]=[CH:17][C:16]([CH:19]=O)=[CH:15][C:13]=3[CH:14]=2)[S:8][CH:9]=1)([CH3:4])([CH3:3])[CH3:2].Cl.[NH2:22]O.CC([O-])=O.[Na+].C(OC(=O)C)(=O)C>C(O)(=O)C.O>[C:1]([C:5]1[N:6]=[C:7]([C:10]2[O:11][C:12]3[CH:18]=[CH:17][C:16]([C:19]#[N:22])=[CH:15][C:13]=3[CH:14]=2)[S:8][CH:9]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 7918Acetic AnhydrideHCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 196038064-Tert-butyl-2-(5-formylbenzofuran-2-yl)thiazole

Product 1

HCID 19092704HCID 19092704, compoundYield 100.6%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

A mixture of 4-tert-butyl-2-(5-formylbenzofuran-2-yl)thiazole (4.46 g), hydroxylamine hydrochloride (3.96 g) and sodium acetate anhydrous (5.0 g) in acetic acid (40 ml) was stirred at ambient temperature for 3 hours. Subsequently, acetic anhydride (13 ml) was added to the mixture. After being stirred for 30 minutes at the same temperature, the reaction mixture was stirred at 120° C. for 2 hours. After being cooled, the mixture was poured into water, followed by collecting by filtration. The precipitates were washed with water and air-dried at ambient temperature. The crude products were washed with petroleum ether to give 4-tert-butyl-2-(5-cyanobenzofuran-2-yl)thiazole (4.44 g).

Workup

  1. stirringAfter being stirred for 30 minutes at the same temperature
  2. stirringthe reaction mixture was stirred at 120° C. for 2 hours
  3. temperatureAfter being cooled
  4. filtrationby collecting by filtration
  5. washThe precipitates were washed with water
  6. customair-dried at ambient temperature
  7. washThe crude products were washed with petroleum ether

Sources & evidence

ORD record
ord-bbfe37a1501c4c938efb6808d2a2dc3a
Source dataset
uspto-grants-1994_03
Patent number
US05296495

Reaction notes

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