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

HRID 2061407

반응식

HRID 2061407 반응식
[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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

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].

후처리

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

출처 및 근거

ORD 기록
ord-b21c1b953f434806a4a55adaee1e662e
출처 데이터셋
uspto-grants-2012_10
특허 번호
US08283351B2

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