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Dimethyl Sulfoxide → N-(5,7-dimethoxy[1,2,4]triazolo-[1,5-a]pyrimidin-2-yl)-2,6-dichlorobenzene-sulfonamide

HRID 411112
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Reaktionsgleichung

Reaktionsgleichung von HRID 411112
[NH2:1][C:2]1[N:14]=[C:5]2[N:6]=[C:7]([O:12][CH3:13])[CH:8]=[C:9]([O:10][CH3:11])[N:4]2[N:3]=1.[Cl:15][C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([Cl:22])[C:17]=1[S:23](Cl)(=[O:25])=[O:24].N1C=CC=CC=1.CS(C)=O>C(#N)C>[CH3:13][O:12][C:7]1[CH:8]=[C:9]([O:10][CH3:11])[N:4]2[N:3]=[C:2]([NH:1][S:23]([C:17]3[C:18]([Cl:22])=[CH:19][CH:20]=[CH:21][C:16]=3[Cl:15])(=[O:25])=[O:24])[N:14]=[C:5]2[N:6]=1
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Komponenten

6

Edukt 4

HCID 679Dimethyl SulfoxideHCID 1049PyridineHCID 5221832,6-DichlorobenzenesulfonylchlorideHCID 11194901[1,2,4]Triazolo[1,5-a]pyrimidin-2-amine, 5,7-dimethoxy-

Produkt 1

HCID 12056874N-(5,7-dimethoxy[1,2,4]triazolo-[1,5-a]pyrimidin-2-yl)-2,6-dichlorobenzene-sulfonamideAusbeute 92 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

2-Amino-5,7-dimethoxy[1,2,4]triazolo[1,5-a]-pyrimidine (0.75 g, 3.8 mmol) and 2,6-dichlorobenzene-sulfonyl chloride (1.86 g, 7.6 mmol) were mixed in dry acetonitrile (15 mL). To this mixture was added dry pyridine (0.61 mL) and dry DMSO (54 μL, 0.7 mmol). The mixture was allowed to stir at room temperature. After 24 hours, the solvent was removed in vacuo, the residue was partitioned between CH2Cl2 (300 mL) and 2N HCl and the solids were collected by vacuum filtration to give a white solid A. The CH2Cl2 was dried (MgSO4) and removed in vacuo to give a white solid B. Both HPLC and NMR indicated that solid A and B are product. The solids were combined to afford the product as a white powder (1.41 g, 92%). mp 211-213° C. Anal: Cacld for C13H11Cl2N5O4S: C, 38.63; H, 2.74; N, 17.33; S, 7.93; found: C, 38.11; H, 2.68; N, 16.83; S, 7.77. 1H NMR (DMSO-d6): δ 12.4 (bs, 1H); 7.64-7.54 (m, 3H); 6.26 (s, 1H); 4.07 (s, 3H); 3.88 (s, 3H).

Aufarbeitung

  1. customthe solvent was removed in vacuo
  2. customthe residue was partitioned between CH2Cl2 (300 mL) and 2N HCl
  3. filtrationthe solids were collected by vacuum filtration
  4. customto give a white solid A
  5. dry with materialThe CH2Cl2 was dried (MgSO4)
  6. customremoved in vacuo
  7. customto give a white solid B

Quellen und Nachweise

ORD-Eintrag
ord-d29b6c1a44644505b2ad52edf33606bb
Quelldatensatz
uspto-grants-2003_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06559101B2

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