Hydrochloric Acid → N-[2-Chloro-4-(4-mesylaminophenylsulphanyl)phenyl]-2-hydroxy-2-methylpropanamide

HRID 1062373Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1062373
O.[OH-].[Li+].[Cl:4][C:5]1[CH:10]=[C:9]([S:11][C:12]2[CH:17]=[CH:16][C:15]([N:18](S(C)(=O)=O)[S:19]([CH3:22])(=[O:21])=[O:20])=[CH:14][CH:13]=2)[CH:8]=[CH:7][C:6]=1[NH:27][C:28](=[O:36])[C:29]([O:32]C(=O)C)([CH3:31])[CH3:30].Cl.C(Cl)Cl>O.CO>[Cl:4][C:5]1[CH:10]=[C:9]([S:11][C:12]2[CH:13]=[CH:14][C:15]([NH:18][S:19]([CH3:22])(=[O:21])=[O:20])=[CH:16][CH:17]=2)[CH:8]=[CH:7][C:6]=1[NH:27][C:28](=[O:36])[C:29]([OH:32])([CH3:31])[CH3:30]

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 6344DichloromethaneHCID 168937Lithium hydroxide, monohydrateHCID 22287442N-[2-Chloro-4-{4-(N,N-dimesylamino)phenylsulphanyl}phenyl]-2-acetoxy-2-methylpropanamide

Produkt 1

HCID 22287414N-[2-Chloro-4-(4-mesylaminophenylsulphanyl)phenyl]-2-hydroxy-2-methylpropanamideAusbeute 86 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittel2×

Versuchsvorschrift

A solution of lithium hydroxide monohydrate (0.177 g) in water (1.8 ml) was added to a stirred solution of N-{2-chloro-4-[4-(N,N-dimesylamino)phenylsulphanyl]phenyl}-2-acetoxy-2-methylpropanamide (Method 26) (0.45 g) in methanol (3.5 ml) and the mixture was stirred at ambient temperature for 4 hours. Water (3 ml) was added and the solution was acidified to pH 2-3 with 1M hydrochloric acid. DCM (20 ml) was added and the organic layer was washed with water (20 ml) and brine, then dried. Volatile material was removed by evaporation and the residue was purified by flash chromatography eluting with 30-70% ethyl acetate/hexane to give the title compound (0.30 g) as a solid. Mp 138-140° C.; NMR (CDCl3): 1.5 (s, 6H), 3.0 (s, 3H), 7.1-7.4 (m, 7H), 8.4 (d, 1H), 9.3 (s, 1H); MS (ESP−):413; EA: found: C, 48.9; H, 4.4; N, 6.5%; C17H19ClN2O4S2 requires C, 49.2; H, 4.6; N, 6.8%.

Aufarbeitung

  1. washthe organic layer was washed with water (20 ml) and brine
  2. customdried
  3. customVolatile material was removed by evaporation
  4. customthe residue was purified by flash chromatography
  5. washeluting with 30-70% ethyl acetate/hexane

Quellen und Nachweise

ORD-Eintrag
ord-113707a709d14b4498a718d8945ca848
Quelldatensatz
uspto-grants-2005_11
Patentnummer
US06960688B2

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