Triethylamine → benzoic acid N'-[2-(2-bromo-phenylsulfanyl)-acetyl]-N'-isopropyl-hydrazide

HRID 2250887Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2250887
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8][CH2:9][C:10]([OH:12])=O.[CH:13]([NH:16][NH:17][C:18](=[O:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)([CH3:15])[CH3:14].C(N(CC)CC)C.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C>CN(C=O)C>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8][CH2:9][C:10]([N:16]([CH:13]([CH3:15])[CH3:14])[NH:17][C:18](=[O:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:12]

Komponenten

7

Edukt 5

HCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 188691-Benzoyl-2-isopropylhydrazineHCID 757711-HydroxybenzotriazoleHCID 23450852-[(2-Bromophenyl)sulfanyl]acetic acid

Produkt 1

HCID 58689908benzoic acid N'-[2-(2-bromo-phenylsulfanyl)-acetyl]-N'-isopropyl-hydrazide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A solution of (2-bromo-phenylsulfanyl)-acetic acid (694 mg, 2.81 mmol) and benzoic acid N′-isopropyl-hydrazide (500 mg, 2.81 mmol) in DMF (10 mL) was treated with triethylamine (1.17 ml, 8.43 mmol), HOBT (455 mg, 3.37 mmol) and EDCI (645 mg, 3.37 mmol) at room temperature overnight. The reaction mixture was partitioned between water and ethyl acetate. The organic layer was successively washed with 1N HCl, aqueous saturated sodium bicarbonate, and brine, then dried over sodium sulfate, filtered and concentrated. Pure product was obtained by crystallization from ethyl acetate (611 mg, 54%).

Aufarbeitung

  1. customThe reaction mixture was partitioned between water and ethyl acetate
  2. washThe organic layer was successively washed with 1N HCl, aqueous saturated sodium bicarbonate, and brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPure product was obtained by crystallization from ethyl acetate (611 mg, 54%)

Quellen und Nachweise

ORD-Eintrag
ord-8c427d1b76ea4dceb672859c97adcee0
Quelldatensatz
uspto-grants-2008_01
Patentnummer
US07317125B2

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