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Triethylamine → 3-(2,6-Dichloro-benzylamino)-4-(1,1-dimethyl-propylamino)-cyclobut-3-ene-1,2-dione

HRID 1956700
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1956700
Cl.[Cl:2][C:3]1[CH:10]=[CH:9][CH:8]=[C:7]([Cl:11])[C:4]=1[CH2:5][NH2:6].C(N(CC)CC)C.C([O:23][C:24]1[C:25](=[O:35])[C:26](=O)[C:27]=1[NH:28][C:29]([CH3:33])([CH3:32])[CH2:30][CH3:31])CCC>O1CCCC1>[Cl:2][C:3]1[CH:10]=[CH:9][CH:8]=[C:7]([Cl:11])[C:4]=1[CH2:5][NH:6][C:26]1[C:25](=[O:35])[C:24](=[O:23])[C:27]=1[NH:28][C:29]([CH3:32])([CH3:33])[CH2:30][CH3:31]
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Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 158388373-Butoxy-4-(1,1-dimethylpropylamino)-cyclobut-3-ene-1,2-dioneHCID 16644432(2,6-Dichlorophenyl)methanamine hydrochloride

Produkt 1

HCID 104974003-(2,6-Dichloro-benzylamino)-4-(1,1-dimethyl-propylamino)-cyclobut-3-ene-1,2-dioneAusbeute 44,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028
Tetrahydrofuran
Lösungsmittel

Versuchsvorschrift

To 2,6-dichlorobenzylamine hydrochloride of Example 4, Step 2 (1.06 g 5.0 mmol) in tetrahydrofuran (10 mL) was added triethyl amine (0.505 g, 5.0 mmol) followed by 3-butoxy-4-(1,1-dimethyl-propylamino)-cyclobut-3-ene-1,2-dione (1.20 g, 5.0 mmol, Example 3) and stirring was continued at room temperature for approximately 16 hours. The reaction mixture was freed of solvent and the residue was triturated successively with water and with diethyl ether, and then dried. The resulting light yellow solid was recrystallized from acetonitrile three times to provide 0.755 g (44%) of the title compound as a white solid: mp 239°-241° C. (dec); 1H NMR (DMSO-d6): δ7.57 (m, 1H), 7.55 (m, 1H), 7.52 (br m, 1H),m 7.43 (m, 1H), 7.30 (s, br, 1H), 5.07 (d, 2H), 1.65 (q, 2H), 1.28 (s, 6H), 0.80 (t, 3H) ppm. IR (KBr): 3250, 1785, 1660 cm-1 ; MS (m/z) 340/342/344 (M+). HPLC indicates a major component (99.7%).

Aufarbeitung

  1. customthe residue was triturated successively with water and with diethyl ether
  2. customdried
  3. customThe resulting light yellow solid was recrystallized from acetonitrile three times

Quellen und Nachweise

ORD-Eintrag
ord-ae7635c53e82473e9cba53e8ed3c61f4
Quelldatensatz
uspto-grants-1998_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05780505

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