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Hydrochloric Acid → C,C,C-Trifluoro-N-{3-[6-(5-fluorobenzothiazol-2-ylmethoxy)-2-methyl-4-oxo-4H-chromen-3-ylmethyl]phenyl}methanesulfonamide

HRID 1684632
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1684632
[F:1][C:2]([F:28])([F:27])[S:3]([NH:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([CH2:13][C:14]2[C:23](=[O:24])[C:22]3[C:17](=[CH:18][CH:19]=[C:20]([OH:25])[CH:21]=3)[O:16][C:15]=2[CH3:26])[CH:8]=1)(=[O:5])=[O:4].C(=O)([O-])[O-].[K+].[K+].Cl[CH2:36][C:37]1[S:38][C:39]2[CH:45]=[CH:44][C:43]([F:46])=[CH:42][C:40]=2[N:41]=1.Cl>CN(C)C=O.CCOCC.O>[F:28][C:2]([F:27])([F:1])[S:3]([NH:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([CH2:13][C:14]2[C:23](=[O:24])[C:22]3[C:17](=[CH:18][CH:19]=[C:20]([O:25][CH2:36][C:37]4[S:38][C:39]5[CH:45]=[CH:44][C:43]([F:46])=[CH:42][C:40]=5[N:41]=4)[CH:21]=3)[O:16][C:15]=2[CH3:26])[CH:8]=1)(=[O:4])=[O:5]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 142042102-(Chloromethyl)-5-fluoro-1,3-benzothiazoleHCID 19039977C,C,C-Trifluoro-N-[3-(6-hydroxy-2-methyl-4-oxo-4H-chromen-3-yl-methyl)phenyl]methanesulfonamide

Produkt 1

HCID 19039946C,C,C-Trifluoro-N-{3-[6-(5-fluorobenzothiazol-2-ylmethoxy)-2-methyl-4-oxo-4H-chromen-3-ylmethyl]phenyl}methanesulfonamide
Ausbeute 97 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 3283Diethyl EtherLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a stirred solution of 1.8 g (4.4 mmole) of the product from Example 126 in 50 mL dimethylformamide was added 2.4 g (17.4 mmole) potassium carbonate. The mixture was stirred at room temperature for 1 hour then 1.2 g (5.72 mmole) 2-(chloromethyl)-5-fluorobenzothiazole was added. The mixture was stirred for 18 hours, poured into water, acidified to ph 1-4 with 1N HCl, and extracted with ethyl acetate. The ethyl acetate extract was washed with water and brine and then dried (MgSO4), and concentrated to give a solid. Trituration with ether afforded 2.45 g (97%) of the title product as a solid, mp 218°-220° C. Analysis calculated for C26H18N2S2O5F4 : C, 53.98; H, 3.14; N, 4.84. Found: C, 53.94; H, 2.91; N, 4.55.

Aufarbeitung

  1. stirringThe mixture was stirred for 18 hours
  2. extractionextracted with ethyl acetate
  3. extractionThe ethyl acetate extract
  4. washwas washed with water and brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated
  7. customto give a solid

Quellen und Nachweise

ORD-Eintrag
ord-3a4997e7629540cea9d569b0cdd3e421
Quelldatensatz
uspto-grants-1997_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05641789

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