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Triethylamine → 4-chloro-3-methoxy-N-(4-methyl-1,2,5-oxadiazol-3-yl)-2,3-dihydro-1-benzothiophene-5-carboxamide 1,1-dioxide

HRID 575915
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 575915
[Cl:1][C:2]1[C:7]2[CH:8]([O:13][CH3:14])[CH2:9][S:10](=[O:12])(=[O:11])[C:6]=2[CH:5]=[CH:4][C:3]=1[C:15]([OH:17])=O.[CH3:18][C:19]1[C:20]([NH2:24])=[N:21][O:22][N:23]=1.C(P1(=O)OP(=O)(CCC)OP(=O)(CCC)O1)CC.C(N(CC)CC)C>C(Cl)Cl.CN(C)C1C=CN=CC=1>[Cl:1][C:2]1[C:7]2[CH:8]([O:13][CH3:14])[CH2:9][S:10](=[O:11])(=[O:12])[C:6]=2[CH:5]=[CH:4][C:3]=1[C:15]([NH:24][C:20]1[C:19]([CH3:18])=[N:23][O:22][N:21]=1)=[O:17]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 8471TriethylamineHCID 286743-Amino-4-methylfurazanHCID 111923Propylphosphonic anhydrideHCID 867154224-Chloro-3-methoxy-2,3-dihydro-1-benzothiophene-5-carboxylic acid 1,1-dioxide

Produkt 1

HCID 867154214-chloro-3-methoxy-N-(4-methyl-1,2,5-oxadiazol-3-yl)-2,3-dihydro-1-benzothiophene-5-carboxamide 1,1-dioxide

Reagenzien, Katalysatoren, Lösungsmittel

2
HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

1.00 g (3.14 mmol) of 4-chloro-3-methoxy-2,3-dihydro-1-benzothiophene-5-carboxylic acid 1,1-dioxide and 0.33 g (3.15 mmol) of 4-methyl-1,2,5-oxadiazol-3-yl-amine were dissolved at room temperature (RT) in 35 ml of CH2Cl2, 3.02 g (4.74 mmol) of 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane 2,4,6-trioxide (50% solution in THF) were added and the mixture was stirred at RT for 1 h. Subsequently, 2.18 ml (15.64 mmol) of triethylamine and 75 mg (0.61 mmol) of 4-dimethylaminopyridine (DMAP) were added and the whole mixture was stirred at RT for 16 h. This was followed by washing with water and twice with 6N hydrochloric acid, drying of the organic phase over Na2SO4 and filtration with suction through silica gel, washing through with 1:2 heptane/ethyl acetate and concentration. Yield 708 mg (63%).

Aufarbeitung

  1. stirringthe whole mixture was stirred at RT for 16 h
  2. washby washing with water and twice with 6N hydrochloric acid
  3. dry with materialdrying of the organic phase over Na2SO4 and filtration with suction through silica gel
  4. washwashing through with 1:2 heptane/ethyl acetate and concentration

Quellen und Nachweise

ORD-Eintrag
ord-17834b21d09d441f81d075bdb2ca113d
Quelldatensatz
uspto-grants-2015_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09035067B2

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