3-Bromo-4-fluorobenzaldehyde → N-[(E)-(3-bromo-4-fluorophenyl)methylideneamino]-2-(4-chloroanilino)acetamide

HRID 2061407

反応式

HRID 2061407 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][CH2:9][C:10]([NH:12][NH2:13])=[O:11])=[CH:4][CH:3]=1.[Br:14][C:15]1[CH:16]=[C:17]([CH:20]=[CH:21][C:22]=1[F:23])[CH:18]=O>C(O)C>[Br:14][C:15]1[CH:16]=[C:17]([CH:20]=[CH:21][C:22]=1[F:23])/[CH:18]=[N:13]/[NH:12][C:10](=[O:11])[CH2:9][NH:8][C:5]1[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=1

参加物

4

反応物 2

HCID 1736043-Bromo-4-fluorobenzaldehydeHCID 3026472371-31-5

生成物 1

HCID 59829142N-[(E)-(3-bromo-4-fluorophenyl)methylideneamino]-2-(4-chloroanilino)acetamide収率 66%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

2-(4-Chlorophenylamino)acetohydrazide (B) (101 mg, 0.51 mmol) and 3-bromo-4-fluorobenzaldehyde (104 mg, 0.51 mmol) were refluxed in ethanol (3 mL) for 15 hours. After cooling to room temperature the precipitate was collected by filtration, washed with ethanol (20 mL) and water (20 mL). Drying in vacuo yielded the title compound (129 mg, 66%) as a colorless powder. 1H NMR δ (ppm) (DMSO-d6): 3.84 and 4.28 (2 H, two d), 6.01 and 6.25 (1 H, two br s), 6.62-6.69 (2 H, m), 7.12-7.17 (2H, m), 7.47-7.51 (1 H, m), 7.77-7.83 (1 H, m), 8.01 and 8.25 (1 H, two s), 8.05-8.12 (1H, m), 11.63 (1 H, two s). LCMS (10 cm_apci_formic) Rt 3.85 min; m/z 384/386/388 [M+H].

後処理

  1. filtrationwas collected by filtration
  2. washwashed with ethanol (20 mL) and water (20 mL)
  3. customDrying in vacuo

出典と根拠

ORDレコード
ord-b21c1b953f434806a4a55adaee1e662e
出典データセット
uspto-grants-2012_10
特許番号
US08283351B2

関連ノート

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