Hydrochloric Acid → 4-[(3,4-dichlorophenoxy)methyl]-N-[(dimethylamino)sulfonyl]-2,5-difluorobenzamide

HRID 1525650Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1525650
Br[CH2:2][C:3]1[C:17]([F:18])=[CH:16][C:6]([C:7]([NH:9][S:10]([N:13]([CH3:15])[CH3:14])(=[O:12])=[O:11])=[O:8])=[C:5]([F:19])[CH:4]=1.[Cl:20][C:21]1[CH:22]=[C:23]([OH:28])[CH:24]=[CH:25][C:26]=1[Cl:27].C(=O)([O-])[O-].[K+].[K+].Cl>CS(C)=O.O>[Cl:20][C:21]1[CH:22]=[C:23]([CH:24]=[CH:25][C:26]=1[Cl:27])[O:28][CH2:2][C:3]1[C:17]([F:18])=[CH:16][C:6]([C:7]([NH:9][S:10]([N:13]([CH3:15])[CH3:14])(=[O:12])=[O:11])=[O:8])=[C:5]([F:19])[CH:4]=1

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 72583,4-DichlorophenolHCID 11430Potassium CarbonateHCID 896195864-(Bromomethyl)-N-[(dimethylamino)sulfonyl]-2,5-difluorobenzamide

Produkt 1

HCID 716162724-[(3,4-dichlorophenoxy)methyl]-N-[(dimethylamino)sulfonyl]-2,5-difluorobenzamideAusbeute 91,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 679Dimethyl SulfoxideLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

To a solution of 4-(bromomethyl)-N-[(dimethylamino)sulfonyl]-2,5-difluorobenzamide (Preparation 1, 40 mg, 0.11 mmol) in dimethylsulfoxide (0.5 mL) was added 3,4-dichlorophenol (18 mg, 0.11 mmol) followed by addition of potassium carbonate (31 mg, 0.22 mmol). The reaction was left to stir at room temperature for 18 hours. The reaction mixture was poured into water (50 mL) and acidified with 2M HCl (2 mL), then extracted with EtOAc (2×50 mL). The combined organic layers were washed with water (20 mL), then dried over magnesium sulfate and evaporated in vacuo to give a colourless glass (44 mg). The solid was then triturated with 1:1 ether:heptane (4 mL), sonicated and the supernatant decanted. The resulting solid was dried in vacuo to give an off-white solid as the title compound (47 mg, 98%).

Aufarbeitung

  1. waitThe reaction was left
  2. extractionextracted with EtOAc (2×50 mL)
  3. washThe combined organic layers were washed with water (20 mL)
  4. dry with materialdried over magnesium sulfate
  5. customevaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-db755c0c62f342ea9a0858e549bb2a21
Quelldatensatz
uspto-grants-2015_07
Patentnummer
US09085517B2

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