Hydroxyamine hydrochloride → HCID 86662402, compound

HRID 389468Notes

Reaction equation

HRID 389468 reaction equation
[Br:1][C:2]1[C:3]([S:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[C:4]([CH:7]=[C:8]([N+:10]([O-:12])=[O:11])[CH:9]=1)[CH:5]=O.Cl.[NH2:19][OH:20]>C(O)(C)C.O>[Br:1][C:2]1[C:3]([S:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[C:4]([CH:7]=[C:8]([N+:10]([O-:12])=[O:11])[CH:9]=1)[CH:5]=[N:19][OH:20]

Participants

5

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 866624003-Bromo-2-tert-butylsulfanyl-5-nitro-benzaldehyde

Product 1

HCID 86662402HCID 86662402, compoundYield 150.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3776IsopropanolSolvent

Procedure

A solution of 3-bromo-2-tert-butylsulfanyl-5-nitro-benzaldehyde (1.2 g, 3.8 mmol) and hydroxylamine hydrochloride (1.2 g, 7.7 mmol) in isopropanol (36 mL) and water (8 mL) was heated to 90° C. for 16 h. The reaction mixture was cooled and concentrated to remove isopropanol. Water was added to the residue, followed by saturated sodium bicarbonate solution until the pH was ˜8.0. The residue was extracted with dichloromethane (2×30 mL). The combined organic fractions were dried with sodium sulfate, filtered, and concentrated to afford 1.9 g of the crude title compound which was used without further purification.

Workup

  1. temperatureThe reaction mixture was cooled
  2. concentrationconcentrated
  3. customto remove isopropanol
  4. additionWater was added to the residue
  5. extractionThe residue was extracted with dichloromethane (2×30 mL)
  6. dry with materialThe combined organic fractions were dried with sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-b5c0aab7056e43688f1173855455eb1e
Source dataset
uspto-grants-2013_02
Patent number
US08378104B2

Reaction notes

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