Triethylamine → (e)-n-[3-Chloro-4-(2-diethylamino-ethoxy)-phenyl]-3-(2-chloro-4-trifluoromethyl-phenyl)-acrylamide

HRID 898563Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 898563
C(N(CC)CC)C.Cl.[Cl:9][C:10]1[CH:11]=[C:12]([NH2:24])[CH:13]=[CH:14][C:15]=1[O:16][CH2:17][CH2:18][N:19]([CH2:22][CH3:23])[CH2:20][CH3:21].[Cl:25][C:26]1[CH:31]=[C:30]([C:32]([F:35])([F:34])[F:33])[CH:29]=[CH:28][C:27]=1/[CH:36]=[CH:37]/[C:38](O)=[O:39].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F>C1COCC1>[Cl:9][C:10]1[CH:11]=[C:12]([NH:24][C:38](=[O:39])/[CH:37]=[CH:36]/[C:27]2[CH:28]=[CH:29][C:30]([C:32]([F:34])([F:33])[F:35])=[CH:31][C:26]=2[Cl:25])[CH:13]=[CH:14][C:15]=1[O:16][CH2:17][CH2:18][N:19]([CH2:22][CH3:23])[CH2:20][CH3:21]

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 5709520HCID 5709520, VerbindungHCID 688758613-Chloro-4-[2-(diethylamino)ethoxy]aniline hydrochloride

Produkt 1

HCID 59691664(e)-n-[3-Chloro-4-(2-diethylamino-ethoxy)-phenyl]-3-(2-chloro-4-trifluoromethyl-phenyl)-acrylamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

0.29 mL (2.10 mmol) of triethylamine was added to a solution of 0.28 g (1.00 mmol) of 3-chloro-4-(2-diethylamino-ethoxy)-phenylamine-hydrochloride (intermediate product Z1b), 0.25 g (1.00 mmol) of (E)-3-(2-chloro-4-trifluoromethyl-phenyl)-acrylic acid (Z37b) and 0.34 g (1.05 mmol) of TBTU in 10 mL abs. THF and the mixture was stirred for 1 hour at RT. The reaction mixture was evaporated down i. vac. and the residue was combined with dichloromethane and water. The org. phase was separated off, washed with sat. aqueous sodium bicarbonate solution and water and evaporated down i. vac. The residue was purified by column chromatography (silica gel, gradient dichloromethane/10% conc. aqueous ammonia in MeOH 100:0→5:95).

Aufarbeitung

  1. customThe reaction mixture was evaporated down i
  2. customphase was separated off
  3. washwashed with sat. aqueous sodium bicarbonate solution and water
  4. customevaporated down i
  5. customThe residue was purified by column chromatography (silica gel, gradient dichloromethane/10% conc. aqueous ammonia in MeOH 100:0→5:95)

Quellen und Nachweise

ORD-Eintrag
ord-98a1bdf123114b2884dca418e10e2487
Quelldatensatz
uspto-grants-2008_04
Patentnummer
US07351719B2

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