2,4-Hexadienoic Acid → N-[4-(3-Bromoanilino)quinazolin-6-yl]hexa-2,4-dienamide

HRID 962617

Reaktionsgleichung

Reaktionsgleichung von HRID 962617
[C:1]([OH:8])(=O)[CH:2]=[CH:3][CH:4]=[CH:5][CH3:6].ClC(OCC(C)C)=O.CN1CCOCC1.[Br:24][C:25]1[CH:26]=[C:27]([NH:31][C:32]2[C:41]3[C:36](=[CH:37][CH:38]=[C:39]([NH2:42])[CH:40]=3)[N:35]=[CH:34][N:33]=2)[CH:28]=[CH:29][CH:30]=1>O1CCCC1.N1C=CC=CC=1>[Br:24][C:25]1[CH:26]=[C:27]([NH:31][C:32]2[C:41]3[C:36](=[CH:37][CH:38]=[C:39]([NH:42][C:1](=[O:8])[CH:2]=[CH:3][CH:4]=[CH:5][CH3:6])[CH:40]=3)[N:35]=[CH:34][N:33]=2)[CH:28]=[CH:29][CH:30]=1

Komponenten

7

Edukt 4

HCID 52512,4-Hexadienoic AcidHCID 79724-MethylmorpholineHCID 62365Isobutyl chloroformateHCID 5328042N4-(3-Bromophenyl)quinazoline-4,6-diamine

Produkt 1

HCID 53794091N-[4-(3-Bromoanilino)quinazolin-6-yl]hexa-2,4-dienamideAusbeute 48,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1049PyridineLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of 0.67 g of 2,4-hexadienoic acid in 10 ml of tetrahydrofuran was cooled in an ice bath. A 0.79 ml portion of isobutyl chloroformate followed by a 0.66 ml portion of N-methyl morpholine were added. After about 1 minute a solution of 1.6 g of N-(3-bromophenyl)-4,6-quinazolindiamine in 10 ml of pyridine was added. The reaction was allowed to come to room temperature and stir overnight. The solvents were removed at reduced pressure and the solid was recrystallized to give 1.0 g of N-[4-[(3-bromophenyl)amino]-6-quinazolinyl]-2,4-hexadienamide: mp=258°-260° C.

Aufarbeitung

  1. additionwere added
  2. customto come to room temperature
  3. customThe solvents were removed at reduced pressure
  4. customthe solid was recrystallized

Quellen und Nachweise

ORD-Eintrag
ord-dd716410943241ecb1fa23f4be07f11b
Quelldatensatz
uspto-grants-1998_06
Patentnummer
US05760041

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