Benzo-1,3-dioxole-5-acetic acid → [2-[(E)-[[2-(1,3-benzodioxol-5-yl)acetyl]hydrazono]methyl]phenyl] 4-(trifluoromethyl)benzenesulfonate

HRID 1795104Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1795104
[F:1][C:2]([F:23])([F:22])[C:3]1[CH:8]=[CH:7][C:6]([S:9]([O:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[CH:19]=[N:20][NH2:21])(=[O:11])=[O:10])=[CH:5][CH:4]=1.[O:24]1[C:28]2[CH:29]=[CH:30][C:31]([CH2:33][C:34](O)=[O:35])=[CH:32][C:27]=2[O:26][CH2:25]1.Cl.C(N=C=NCCCN(C)C)C>CN(C=O)C.CN(C)C1C=CN=CC=1.C(Cl)Cl>[F:23][C:2]([F:1])([F:22])[C:3]1[CH:4]=[CH:5][C:6]([S:9]([O:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2/[CH:19]=[N:20]/[NH:21][C:34](=[O:35])[CH2:33][C:31]2[CH:30]=[CH:29][C:28]3[O:24][CH2:25][O:26][C:27]=3[CH:32]=2)(=[O:11])=[O:10])=[CH:7][CH:8]=1

Komponenten

7

Edukt 3

HCID 76115Benzo-1,3-dioxole-5-acetic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 738686872-[Hydrazonomethyl]phenyl 4-(trifluoromethyl)benzenesulfonate

Produkt 1

HCID 11443535[2-[(E)-[[2-(1,3-benzodioxol-5-yl)acetyl]hydrazono]methyl]phenyl] 4-(trifluoromethyl)benzenesulfonate

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6228DimethylformamideLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A solution of 2-[hydrazonomethyl]phenyl 4-(trifluoromethyl)benzenesulfonate (150 mg, 0.44 mmol) and 1,3-benzodioxol-5-ylacetic acid (1.2 equiv) in DMF (1 mL) is treated with a solution of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (EDC) (167 mg, 0.87 mmol) and 4-dimethylaminopyridine (DMAP) (106 mg, 0.87 mmol) in CH2Cl2 (10 mL). The solution is shaken overnight on an orbital shaker. The solution is evaporated to dryness using a speed. Water is added to the mixture, which is then sonicated to give a solid. The solid is filtered and washed with a large amount of water. A small amount of methanol is added and the mixture sonicated. The resulting solid is filtered and washed with more methanol to yield pure 2-((E)-{2-[2-(1,3-benzodioxol-5-yl)acetyl]hydrazono}methyl)phenyl 4-(trifluoromethyl)benzenesulfonate. The yield is 169 mg, 77%. 1H NMR (400 MHz, DMSO) □ 11.48 (2s, 1H), 8.01 (m, 6H), 7.12 (m, 6H), 5.99 (2s, 2H), 3.62 (2s, 2H). ESI− for C23H17F3N2O6S, m/z 505, (M−H)−.

Aufarbeitung

  1. customThe solution is evaporated to dryness
  2. additionWater is added to the mixture, which
  3. customis then sonicated
  4. customto give a solid
  5. filtrationThe solid is filtered
  6. washwashed with a large amount of water
  7. additionA small amount of methanol is added
  8. customthe mixture sonicated
  9. filtrationThe resulting solid is filtered
  10. washwashed with more methanol

Quellen und Nachweise

ORD-Eintrag
ord-4ffdc974155346f6923c61c5c40a4930
Quelldatensatz
uspto-grants-2006_04
Patentnummer
US07026339B2

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