Hydroxyamine hydrochloride → 7-Bromo-benzo[1,2,5]thiadiazole-4-carbaldehyde oxime

HRID 1505243Notes

Reaction equation

HRID 1505243 reaction equation
[Br:1][C:2]1[C:10]2[C:6](=[N:7][S:8][N:9]=2)[C:5]([CH:11]=O)=[CH:4][CH:3]=1.Cl.[NH2:14][OH:15].C(=O)([O-])O.[Na+]>C(O)C.C(OCC)(=O)C.O>[Br:1][C:2]1[C:10]2[C:6](=[N:7][S:8][N:9]=2)[C:5]([CH:11]=[N:14][OH:15])=[CH:4][CH:3]=1

Participants

7

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 516892Sodium BicarbonateHCID 584979627-Bromo-2,1,3-benzothiadiazole-4-carboxaldehyde

Product 1

HCID 1363510697-Bromo-benzo[1,2,5]thiadiazole-4-carbaldehyde oximeYield 94.2%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 7-bromo-benzo[1,2,5]thiadiazole-4-carbaldehyde (Example 5.3) (16.65 g) in ethanol (150 ml) were added hydroxylamine hydrochloride (9.52 g), sodium hydrogen carbonate (11.51 g) and water (15 ml). The reaction mixture was stirred at ambient temperature for 16 hours. The reaction mixture was diluted with ethyl acetate (1500 ml) and water (400 ml). After separation of the phases, the aqueous layer was extracted with ethyl acetate (200 ml). The combined organic layers were washed with water (200 ml) and brine (200 ml), dried over sodium sulfate and concentrated to give 7-bromo-benzo[1,2,5]thiadiazole-4-carbaldehyde oxime (16.65 g) as a brown solid. 1H-NMR (DMSO-d6, 400 MHz): 11.94 (s, 1H), 8.66 (s, 1H), 8.09-9.90 (m, 2H) ppm.

Workup

  1. customAfter separation of the phases
  2. extractionthe aqueous layer was extracted with ethyl acetate (200 ml)
  3. washThe combined organic layers were washed with water (200 ml) and brine (200 ml)
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-c5e54507ebf749f59121128ce246dd3d
Source dataset
uspto-grants-2015_12
Patent number
US09216973B2

Reaction notes

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