Pyridine → methyl 4-(N,N-dimethylsulfamoyl)amino-2-chlorobenzoate

HRID 24723

Reaktionsgleichung

Reaktionsgleichung von HRID 24723
N1C=CC=CC=1.[NH2:7][C:8]1[CH:17]=[CH:16][C:11]([C:12]([O:14][CH3:15])=[O:13])=[C:10]([Cl:18])[CH:9]=1.[CH3:19][N:20]([CH3:25])[S:21](Cl)(=[O:23])=[O:22]>C(Cl)Cl.CN(C1C=CN=CC=1)C>[CH3:19][N:20]([CH3:25])[S:21]([NH:7][C:8]1[CH:17]=[CH:16][C:11]([C:12]([O:14][CH3:15])=[O:13])=[C:10]([Cl:18])[CH:9]=1)(=[O:23])=[O:22]

Komponenten

6

Edukt 3

HCID 1049PyridineHCID 83372Dimethylsulphamoyl chlorideHCID 11839197Methyl 4-Amino-2-chlorobenzoate

Produkt 1

HCID 22571711methyl 4-(N,N-dimethylsulfamoyl)amino-2-chlorobenzoate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

Pyridine (0.4 mL) was added to a solution of methyl 4-amino-2-chlorobenzoate (0.3 g) in CH2Cl2 (10 mL) at 0° C. under N2. N,N-Dimethylsulfamoyl chloride (0.21 mL) was added and the mixture was stirred at room temperature for 16 hours and refluxed for 5 hours. DMAP (0.4 g) was added and the mixture was stirred for 3 hours. The mixture was diluted with CH2Cl2 (100 mL), washed successively with 1N HCl, brine, satd. NaHCO3 and brine, dried and evaporated. The residue was purified by flash column chromatography (silica gel; eluent: EtOAc/hexane 1:3) to give 0.31 g of methyl 4-(N,N-dimethylsulfamoyl)amino-2-chlorobenzoate. ESMS: m/z 293 (MH+)

Aufarbeitung

  1. temperaturerefluxed for 5 hours
  2. stirringthe mixture was stirred for 3 hours
  3. washwashed successively with 1N HCl, brine
  4. dry with materialNaHCO3 and brine, dried
  5. customevaporated
  6. customThe residue was purified by flash column chromatography (silica gel; eluent: EtOAc/hexane 1:3)

Quellen und Nachweise

ORD-Eintrag
ord-b4dc9b02a77c414a895c085f1167af81
Quelldatensatz
uspto-grants-2005_02
Patentnummer
US06855843B2

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