Triethylamine → N-(2-diethylamino-ethyl)-4-(bismethanesulfonylamino)-2-methoxy-benzamide

HRID 2262353Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2262353
[NH2:1][C:2]1[CH:17]=[CH:16][C:5]([C:6]([NH:8][CH2:9][CH2:10][N:11]([CH2:14][CH3:15])[CH2:12][CH3:13])=[O:7])=[C:4]([O:18][CH3:19])[CH:3]=1.C(N(CC)CC)C.[CH3:27][S:28](Cl)(=[O:30])=[O:29].C(=O)(O)[O-].[Na+]>C(Cl)Cl>[CH2:14]([N:11]([CH2:12][CH3:13])[CH2:10][CH2:9][NH:8][C:6](=[O:7])[C:5]1[CH:16]=[CH:17][C:2]([N:1]([S:28]([CH3:27])(=[O:30])=[O:29])[S:28]([CH3:27])(=[O:30])=[O:29])=[CH:3][C:4]=1[O:18][CH3:19])[CH3:15]

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 773744-Amino-N-[2-(diethylamino)ethyl]-2-methoxybenzamideHCID 516892Sodium Bicarbonate

Produkt 1

HCID 66934940N-(2-diethylamino-ethyl)-4-(bismethanesulfonylamino)-2-methoxy-benzamideAusbeute 100,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

265 mg (1 mmol) of 4-amino-N-(2-diethylamino-ethyl)-2-methoxy-benzamide is introduced into 15 ml of methylene chloride and mixed in succession with 111 mg (1.1 mmol) of triethylamine and 126 mg (1.1 mmol) of methanesulfonic acid chloride. It is stirred for 2 hours at room temperature and then allowed to stand overnight. It is then mixed with 25 ml of saturated sodium bicarbonate solution and shaken out three times with 25 ml each of methylene chloride. The collected organic phase is dried, filtered and concentrated by evaporation. The residue is chromatographed on 10 g of basic silica gel (Isolute flash Si NH2) with a gradient from cyclohexane:ethyl acetate=100:0 to 50:50. 232 mg (52.6% of theory) of N-(2-diethylamino-ethyl)-4-(bismethanesulfonylamino)-2-methoxy-benzamide with a melting point of 144.1° C. is obtained.

Aufarbeitung

  1. waitto stand overnight
  2. customThe collected organic phase is dried
  3. filtrationfiltered
  4. concentrationconcentrated by evaporation
  5. customThe residue is chromatographed on 10 g of basic silica gel (Isolute flash Si NH2) with a gradient from cyclohexane

Quellen und Nachweise

ORD-Eintrag
ord-d7db9b057cd24ffa91942e1dcf43f602
Quelldatensatz
uspto-grants-2010_12
Patentnummer
US07850948B2

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