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

HRID 536419ノート

反応式

HRID 536419 の反応式
[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

参加物

7

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 702Ethanol溶媒HCID 962Water溶媒2 回HCID 8857Ethyl Acetate溶媒

実験手順

To a solution of 7-bromo-benzo[1,2,5]thiadiazole-4-carbaldehyde (16.65 g) (Example I3) 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.

後処理

  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

出典と根拠

ORDレコード
ord-68cf854d5dae4149bcc923b1095b1fb2
出典データセット
uspto-grants-2014_10
特許番号
US08859592B2

反応ノート

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