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

HRID 1505243노트

반응식

HRID 1505243 반응식
[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

참가 물질

7

반응물 3

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

생성물 1

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

시약·촉매·용매 3

HCID 702Ethanol용매HCID 962Water용매2회HCID 8857Ethyl Acetate용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-c5e54507ebf749f59121128ce246dd3d
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09216973B2

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