Triethylamine → 1-{3-[(2-Naphthyl)methoxy]-5-nitrobenzoyl)-2-benzoylhydrazine

HRID 431387Notes

Reaction equation

HRID 431387 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][O:12][C:13]1[CH:14]=[C:15]([CH:20]=[C:21]([N+:23]([O-:25])=[O:24])[CH:22]=1)[C:16]([NH:18][NH2:19])=[O:17].C(N(CC)CC)C.[C:33](Br)(=[O:40])[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1>CC(N(C)C)=O>[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][O:12][C:13]1[CH:14]=[C:15]([CH:20]=[C:21]([N+:23]([O-:25])=[O:24])[CH:22]=1)[C:16]([NH:18][NH:19][C:33](=[O:40])[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)=[O:17]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 12056Benzoyl bromideHCID 18763439HCID 18763439, compound

Product 1

HCID 187634381-{3-[(2-Naphthyl)methoxy]-5-nitrobenzoyl)-2-benzoylhydrazine

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

To a stirred solution of 3-[(2-naphthyl)methoxy]-5-nitrobenzhydrazide (0.30 g, 0.89 mmol) and triethylamine (0.14 mL, 0.98 mmol) in DMA (25 mL) at room temperature was added benzoyl bromide (0.11 mL, 0.89 mmol), and stirring was continued overnight. Yellowish solution was poured onto ice-water (50 g) and set aside for 24 h. Precipitate formed was filtered, washed with water, and air-dried. Off-white solid, yield 0.34 g (87%). 1H NMR (DMSO-d6, 400 MHz), δ: 10.92 (s, 1H); 10.66 (s, 1H); 8.12-7.89 (m, 8H); 7.67-7.50 (m, 6H); 5.53 (s, 2H).

Workup

  1. additionYellowish solution was poured onto ice-water (50 g)
  2. waitset aside for 24 h
  3. customPrecipitate formed
  4. filtrationwas filtered
  5. washwashed with water
  6. customair-dried

Sources & evidence

ORD record
ord-b97485d6ae354f0388a93944eee82029
Source dataset
uspto-grants-2003_12
Patent number
US06656971B2

Reaction notes

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