Sodium hydride → methyl 3-chloro(N-(4-chlorobenzenesulphonyl)-N-methylaminomethyl)thiophene-2-carboxylate

HRID 901954

Reaktionsgleichung

Reaktionsgleichung von HRID 901954
[H-].[Na+].[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([S:10]([NH:13][CH3:14])(=[O:12])=[O:11])=[CH:6][CH:5]=1.Br[CH2:16][C:17]1[C:18]([Cl:26])=[C:19]([C:22]([O:24][CH3:25])=[O:23])[S:20][CH:21]=1.S([O-])(O)(=O)=O.[K+]>CN(C=O)C>[Cl:26][C:18]1[C:17]([CH2:16][N:13]([S:10]([C:7]2[CH:8]=[CH:9][C:4]([Cl:3])=[CH:5][CH:6]=2)(=[O:12])=[O:11])[CH3:14])=[CH:21][S:20][C:19]=1[C:22]([O:24][CH3:25])=[O:23]

Komponenten

6

Edukt 4

HCID 24758Sodium hydrideHCID 2329924-Chloro-N-methylbenzenesulfonamideHCID 516920Potassium bisulfateHCID 18376575Methyl 4-(bromomethyl)-3-chlorothiophene-2-carboxylate

Produkt 1

HCID 69208322methyl 3-chloro(N-(4-chlorobenzenesulphonyl)-N-methylaminomethyl)thiophene-2-carboxylateAusbeute 102,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Sodium hydride (60% dispersion, 150 mg, 3.8 mmol) was added to a solution of 4-chloro-N-methylbenzenesulfonamide (640 mg, 3.1 mmol) in DMF (12 ml) while cooling in an ice/water bath. After stirring for 15 min the mixture was allowed to warm to room temperature and stirred for a further 30 min. Methyl 4-bromomethyl-3-chlorothiophene-2-carboxylate (1.08 g, 4.0 mmol) was added and the mixture was stirred for 18 h. 0.3N Potassium hydrogen sulphate solution was added and the mixture evaporated. The mixture was extracted with ethyl acetate and the organic extract was washed with brine, dried and reduced. Chromatography (25% EtOAc/75% 60-80 pet ether) yielded methyl 3-chloro(N-(4-chlorobenzenesulphonyl)-N-methylaminomethyl)thiophene-2-carboxylate (1.25 g, 79%) as a white solid.

Aufarbeitung

  1. temperaturewhile cooling in an ice/water bath
  2. stirringstirred for a further 30 min
  3. stirringthe mixture was stirred for 18 h
  4. customthe mixture evaporated
  5. extractionThe mixture was extracted with ethyl acetate
  6. extractionthe organic extract
  7. washwas washed with brine
  8. customdried

Quellen und Nachweise

ORD-Eintrag
ord-337ed5aeaf244c55825edb2de5c57ca4
Quelldatensatz
uspto-grants-2008_04
Patentnummer
US07365065B2

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