Hydroxyamine hydrochloride → HCID 86662413, compound

HRID 389521Notes

Reaction equation

HRID 389521 reaction equation
[Br:1][C:2]1[C:3]([S:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[C:4]([CH:7]=[C:8]([F:10])[CH:9]=1)[CH:5]=O.Cl.[NH2:17][OH:18]>C(O)(C)C.O>[Br:1][C:2]1[C:3]([S:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[C:4]([CH:7]=[C:8]([F:10])[CH:9]=1)[CH:5]=[N:17][OH:18]

Participants

5

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 86662414HCID 86662414, compound

Product 1

HCID 86662413HCID 86662413, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3776IsopropanolSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 3-bromo-2-tert-butylsulfanyl-5-fluorobenzaldehyde (4 g, 13.7 mmol) and hydroxylamine hydrochloride in isopropanol (160 mL) and water (33 mL) was heated to 90° C. for 16 h. The reaction mixture was cooled and 2-propanol was removed in vacuo. Water was added to residue, followed by saturated aqueous sodium bicarbonate until the pH was ˜8. The mixture was extracted with dichloromethane (2×30 mL). The combined organic fractions were dried sodium sulfate, filtered, and concentrated to afford 3.8 g of the crude title compound, which was used without further purification.

Workup

  1. temperatureThe reaction mixture was cooled
  2. custom2-propanol was removed in vacuo
  3. additionWater was added to residue
  4. extractionThe mixture was extracted with dichloromethane (2×30 mL)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-d16a08bcbde14eb5ad44a7b5224bebe8
Source dataset
uspto-grants-2013_02
Patent number
US08378104B2

Reaction notes

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