Hydrochloric Acid → N-(5-chloro-thiazol-2-yl)-3-cyano-4-fluorobenzenesulfonamide

HRID 46285

Reaktionsgleichung

Reaktionsgleichung von HRID 46285
Cl.[NH2:2][C:3]1[S:4][C:5]([Cl:8])=[CH:6][N:7]=1.N1C=CC=CC=1.[C:15]([C:17]1[CH:18]=[C:19]([S:24](Cl)(=[O:26])=[O:25])[CH:20]=[CH:21][C:22]=1[F:23])#[N:16].Cl>ClCCl>[Cl:8][C:5]1[S:4][C:3]([NH:2][S:24]([C:19]2[CH:20]=[CH:21][C:22]([F:23])=[C:17]([C:15]#[N:16])[CH:18]=2)(=[O:25])=[O:26])=[N:7][CH:6]=1

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 1487432-Amino-5-chlorothiazole hydrochlorideHCID 27789083-Cyano-4-fluorobenzenesulfonyl chloride

Produkt 1

HCID 59436522N-(5-chloro-thiazol-2-yl)-3-cyano-4-fluorobenzenesulfonamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a stirred mixture of 2-amino-5-chlorothiazole-hydrochloride (3.76 g, 22.0 mmol) in dichloromethane (20 ml) was added pyridine (8.09 ml, 100 mmol). 3-cyano-4-fluorobenzenesulfonyl chloride (4.39 g, 20 mmol) dissolved in dichloromethane (5 mL) and was added to the reaction mixture dropwise at room temperature. After stirring for 48 hours at room temperature, 1 N HCl (100 mL) was poured into the reaction and the mixture was extracted with dichloromethane/methanol (v/v=95/5, 100 ml) three times. The collected organic layer was evaporated in vacuo and dried over MgSO4 to obtain the crude residue. The crude residue was washed with dichloromethane (10 mL) and filtered to afford pale yellow solid as the title compound. LCMS Rt=1.39 minutes MS m/z 318 [M35ClH]+, 320 [M37ClH]+ 1HNMR (d6-DMSO): δ 7.59 (s, 1H), 7.66-7.73 (m, 1H), 8.15-8.21 (m, 1H), 8.33-8.37 (m, 1H).

Aufarbeitung

  1. additionwas added to the reaction mixture dropwise at room temperature
  2. extractionthe mixture was extracted with dichloromethane/methanol (v/v=95/5, 100 ml) three times
  3. customThe collected organic layer was evaporated in vacuo
  4. dry with materialdried over MgSO4
  5. customto obtain the crude residue
  6. washThe crude residue was washed with dichloromethane (10 mL)
  7. filtrationfiltered

Quellen und Nachweise

ORD-Eintrag
ord-98dd9396fb8244ca8ca23e61a05fbf26
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08541588B2

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