Hydrochloric Acid → 3-Chloro-N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-2-[(2-oxotetrahydro-3-furanylidene)methyl]benzenesulfonamide

HRID 34882Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 34882
[Cl:1][C:2]1[C:3]([CH:12]=[C:13]2[CH2:17][CH2:16][O:15][C:14]2=[O:18])=[C:4]([S:8]([NH2:11])(=[O:10])=[O:9])[CH:5]=[CH:6][CH:7]=1.[CH3:19][O:20][C:21]1[CH:26]=[C:25]([O:27][CH3:28])[N:24]=[C:23]([NH:29][C:30](=O)[O:31]C2C=CC=CC=2)[N:22]=1.N12CCCN=C1CCCCC2.Cl>C(#N)C.O>[Cl:1][C:2]1[C:3]([CH:12]=[C:13]2[CH2:17][CH2:16][O:15][C:14]2=[O:18])=[C:4]([S:8]([NH:11][C:30]([NH:29][C:23]2[N:22]=[C:21]([O:20][CH3:19])[CH:26]=[C:25]([O:27][CH3:28])[N:24]=2)=[O:31])(=[O:9])=[O:10])[CH:5]=[CH:6][CH:7]=1

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 10945667Carbamic acid, N-(4,6-dimethoxy-2-pyrimidinyl)-, phenyl esterHCID 53966879HCID 53966879, Verbindung

Produkt 1

HCID 543779873-Chloro-N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-2-[(2-oxotetrahydro-3-furanylidene)methyl]benzenesulfonamideAusbeute 85,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

To a stirred suspension of 0.15 g (0.0005 mol) of the product of Example 7 and 0.21 g (0.0008 mol) of (4,6-dimethoxy-2-pyrimidinyl)carbamic acid, phenyl ester in 1 mL dry acetonitrile under nitrogen was added dropwise 0.12 mL (0.12 g, 0.0008 mol) of 1,8-diazabicyclo[5.4.0]undec-7-ene. The mixture was stirred at room temperature for 1 hour and was then diluted with water and acidified with 1N aqueous hydrochloric acid. The resulting precipitate was collected by filtration and washed well with water and ether to yield 0.2 g (83%) of the title compound: m.p. 212°-216° (dec); IR (nujol) 3410, 1765, 1605, 1365, 1340, 1155 cm-1 ; NMR (CDCl3, 200 MHz) δ 2.7-2.8 (2H, m), 3.94 (6H, s), 4.1-4.2 (2H, m), 5.84 (1H, s), 7.2-7.8 (3H, m), 8.25 (1H, m).

Aufarbeitung

  1. filtrationThe resulting precipitate was collected by filtration
  2. washwashed well with water and ether

Quellen und Nachweise

ORD-Eintrag
ord-e7ad624552314958bc648ad795e232d1
Quelldatensatz
uspto-grants-1988_08
Patentnummer
US04764207

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