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Triethylamine → N-[4-[2-(Dimethylamino)ethoxy]benzyl]-5-dimethylaminosulfonyl 2-methoxybenzamide

HRID 703532
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 703532
[CH3:1][N:2]([CH3:17])[S:3]([C:6]1[CH:7]=[CH:8][C:9]([O:15][CH3:16])=[C:10]([CH:14]=1)[C:11]([OH:13])=O)(=[O:5])=[O:4].C(N(CC)CC)C.ClC(OCC)=O.[CH3:31][N:32]([CH3:44])[CH2:33][CH2:34][O:35][C:36]1[CH:43]=[CH:42][C:39]([CH2:40][NH2:41])=[CH:38][CH:37]=1>O1CCCC1>[CH3:31][N:32]([CH3:44])[CH2:33][CH2:34][O:35][C:36]1[CH:43]=[CH:42][C:39]([CH2:40][NH:41][C:11](=[O:13])[C:10]2[CH:14]=[C:6]([S:3]([N:2]([CH3:1])[CH3:17])(=[O:4])=[O:5])[CH:7]=[CH:8][C:9]=2[O:15][CH3:16])=[CH:38][CH:37]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 88349p-(2-(Dimethylamino)ethoxy)benzylamineHCID 135768955-(N,N-dimethylsulfamoyl)-2-methoxybenzoic acid

Produkt 1

HCID 15622788N-[4-[2-(Dimethylamino)ethoxy]benzyl]-5-dimethylaminosulfonyl 2-methoxybenzamideAusbeute 91,4 %

Reagenzien, Katalysatoren, Lösungsmittel

1
HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a cooled suspension of 3.20 g of 5-dimethylaminosulfonyl-2-methoxybenzoic acid in 10 ml of tetrahydrofuran were successively added dropwise 1.25 g of triethylamine and 1.34 g of ethyl chloroformate with stirring. The mixture was stirred at the same temperature for 30 minutes and then a solution of 2.00 g of 4-[2-(dimethylamino)ethoxy]benzylamine in 10 ml of tetrahydrofuran was added dropwise with stirring. The mixture was stirred at room temperature for 2 hours and the solvent was evaporated. Hydrochloric acid (10%) was added to the residue and the aqueous solution was washed with ethyl acetate. The aqueous layer was made alkaline with potassium carbonate and was extracted with ethyl acetate. The extract was dried and evaporated. The residue was washed with isopropyl ether to give 4.10 g of colorless crystals, which were recrystallized from a mixture of ethyl acetate and ether to give colorless needles, m.p. 99.5°-100.5° C.

Aufarbeitung

  1. stirringThe mixture was stirred at the same temperature for 30 minutes
  2. stirringwith stirring
  3. stirringThe mixture was stirred at room temperature for 2 hours
  4. customthe solvent was evaporated
  5. additionHydrochloric acid (10%) was added to the residue
  6. washthe aqueous solution was washed with ethyl acetate
  7. extractionwas extracted with ethyl acetate
  8. customThe extract was dried
  9. customevaporated
  10. washThe residue was washed with isopropyl ether

Quellen und Nachweise

ORD-Eintrag
ord-0998027b0f7c46eb9408bc62bd472629
Quelldatensatz
uspto-grants-1991_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04983633

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