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Triethylamine → methyl 4-(1,1-dioxidotetrahydro-2H-1,2-thiazin-2-yl)-1H-benzimidazole-6-carboxylate

HRID 852621
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 852621
Cl[CH2:2][CH2:3][CH2:4][CH2:5][S:6]([NH:9][C:10]1[C:18]2[N:17]=[CH:16][NH:15][C:14]=2[CH:13]=[C:12]([C:19]([O:21][CH3:22])=[O:20])[CH:11]=1)(=[O:8])=[O:7].CCN(CC)CC>CCO>[O:7]=[S:6]1(=[O:8])[CH2:5][CH2:4][CH2:3][CH2:2][N:9]1[C:10]1[C:18]2[N:17]=[CH:16][NH:15][C:14]=2[CH:13]=[C:12]([C:19]([O:21][CH3:22])=[O:20])[CH:11]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

4

Edukt 2

HCID 8471TriethylamineHCID 69360119methyl 4-{[(4-chlorobutyl)sulfonyl]amino}-1H-benzimidazole-6-carboxylate

Produkt 1

HCID 69357660methyl 4-(1,1-dioxidotetrahydro-2H-1,2-thiazin-2-yl)-1H-benzimidazole-6-carboxylateAusbeute 25 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

To a solution of methyl 4-{[(4-chlorobutyl)sulfonyl]amino}-1H-benzimidazole-6-carboxylate (D252) (1 g, 3.23 mmol, 1 equiv) in EtOH (50 ml) was added NEt3 (2 ml, excess) and the resulting solution was stirred at 70° C. for 2 days. then cooled to room temperature and concentrated in vacuo. The residue was dissolved in AcOEt and the organic phase was washed with a 5% aqueous citric acid solution. The aqueous phase was saturated with NaCl and extracted twice with AcOEt. The combined organic phases were dried over MgSO4 and concentrated in vacuo. Purification of the residue by flash chromatography on silica gel (CH2Cl2/MeOH: 96/4 to 90/10) gave methyl 4-(1,1-dioxidotetrahydro-2H-1,2-thiazin-2-yl)-1H-benzimidazole-6-carboxylate (D253) (250 mg, 25%) as a pale yellow solid. [M+H]+=310.3, RT=2.11 min.

Aufarbeitung

  1. temperaturethen cooled to room temperature
  2. concentrationconcentrated in vacuo
  3. dissolutionThe residue was dissolved in AcOEt
  4. washthe organic phase was washed with a 5% aqueous citric acid solution
  5. extractionextracted twice with AcOEt
  6. dry with materialThe combined organic phases were dried over MgSO4
  7. concentrationconcentrated in vacuo
  8. customPurification of the residue by flash chromatography on silica gel (CH2Cl2/MeOH: 96/4 to 90/10)

Quellen und Nachweise

ORD-Eintrag
ord-18b70689c5024718b1a9b841eacf5174
Quelldatensatz
uspto-grants-2007_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07253198B2

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