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Triethylamine → N-[2-methyl-5-(3-morpholinobenzamido)phenyl]thiophene-2-carboxamide

HRID 1828724
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1828724
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6](Cl)=[O:7].[NH2:9][C:10]1[CH:11]=[C:12]([NH:17][C:18](=[O:31])[C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([N:25]3[CH2:30][CH2:29][O:28][CH2:27][CH2:26]3)[CH:20]=2)[CH:13]=[CH:14][C:15]=1[CH3:16].C(N(CC)CC)C>C(Cl)Cl>[CH3:16][C:15]1[CH:14]=[CH:13][C:12]([NH:17][C:18](=[O:31])[C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([N:25]3[CH2:26][CH2:27][O:28][CH2:29][CH2:30]3)[CH:20]=2)=[CH:11][C:10]=1[NH:9][C:6]([C:2]1[S:1][CH:5]=[CH:4][CH:3]=1)=[O:7]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 789282-Thiophenecarbonyl chlorideHCID 11301391N-(3-amino-4-methylphenyl)-3-morpholinobenzamide

Produkt 1

HCID 11327642N-[2-methyl-5-(3-morpholinobenzamido)phenyl]thiophene-2-carboxamideAusbeute 33,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Thiophene-2-carbonyl chloride (0.069 g) was added to a stirred suspension of N-(3-amino-4-methylphenyl)-3-morpholinobenzamide (0.104 g), triethylamine (0.15 ml) and methylene chloride (20 ml) and the resultant mixture was stirred at ambient temperature for 4 hours. The organic phase was washed with water and with a saturated aqueous sodium bicarbonate solution, dried (MgSO4) and evaporated. The residue was dissolved in methylene chloride (2 ml) and diethyl ether (20 ml) was added to give a precipitate which was isolated by filtration, washed with diethyl ether and dried. There was thus obtained the title compound (0.047 g); NMR Spectrum: (DMSOd6) 2.18 (t, 3H), 3.18 (t, 4H), 3.76 (t, 4H), 7.14 (d, 1H), 7.20 (m, 2H), 7.38 (m, 2H), 7.41 (s, 1H), 7.58 (m, 1H), 7.78 (s, 1H), 7.82 (d, 1H), 7.98 (d, 1H), 9.93 (s, 1H), 10.13 (s, 1H); Mass Spectrum: M+H+ 422.

Aufarbeitung

  1. washThe organic phase was washed with water and with a saturated aqueous sodium bicarbonate solution
  2. dry with materialdried (MgSO4)
  3. customevaporated
  4. dissolutionThe residue was dissolved in methylene chloride (2 ml)
  5. additiondiethyl ether (20 ml) was added
  6. customto give a precipitate which
  7. customwas isolated by filtration
  8. washwashed with diethyl ether
  9. customdried

Quellen und Nachweise

ORD-Eintrag
ord-4b720b2560e94275967193d52a220c5c
Quelldatensatz
uspto-grants-2006_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07060700B2

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