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

HRID 2061407

Reaction equation

HRID 2061407 reaction equation
[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

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

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].

Workup

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

Sources & evidence

ORD record
ord-b21c1b953f434806a4a55adaee1e662e
Source dataset
uspto-grants-2012_10
Patent number
US08283351B2

Linked notes

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