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Triethylamine → 2,2-Dimethyl-2,3-dihydro-7-[N-methyl-N-(4-tert-butylphenylthiosulfenyl)carbamoyloxy] benzofuran

HRID 1112407
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1112407
[CH3:1][C:2]1([CH3:12])[CH2:6][C:5]2[CH:7]=[CH:8][CH:9]=[C:10]([OH:11])[C:4]=2[O:3]1.[CH3:13][N:14]([S:18][S:19][C:20]1[CH:25]=[CH:24][C:23]([C:26]([CH3:29])([CH3:28])[CH3:27])=[CH:22][CH:21]=1)[C:15](F)=[O:16].C(N(CC)CC)C>O1CCOCC1.O>[CH3:1][C:2]1([CH3:12])[CH2:6][C:5]2[CH:7]=[CH:8][CH:9]=[C:10]([O:11][C:15](=[O:16])[N:14]([CH3:13])[S:18][S:19][C:20]3[CH:25]=[CH:24][C:23]([C:26]([CH3:27])([CH3:29])[CH3:28])=[CH:22][CH:21]=3)[C:4]=2[O:3]1
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Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 152782,3-Dihydro-2,2-dimethyl-7-benzofuranolHCID 23333006N-Methyl-N(4-t-Butylphenylthiosulfenyl) Carbamoyl Fluoride

Produkt 1

HCID 227640422,2-Dimethyl-2,3-dihydro-7-[N-methyl-N-(4-tert-butylphenylthiosulfenyl)carbamoyloxy] benzofuranAusbeute 39,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962
Water
Lösungsmittel
HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

To a solution of 4.0 g (0.024 m) of 2,2-dimethyl-2,3-dihydrobenzofuran-7-ol and 6.56 g (0.024 m) of N-methyl-N-(p-tert-butylphenylthiosulfenyl)carbamoyl fluoride in 25 ml of dioxane was added 2.45 g (0.024 m) of triethylamine. After 24 hours the reaction mixture was diluted with 200 ml of water and the product was extracted in ethylacetate. The organic extract was washed in turn with diluted sodium hydroxide and water, dried over MgSO4 and concentrated under reduced pressure. The product was crystallized from isopropyl ether to yield 4.0 g of a white solid, m.p. 150°-151° C.

Aufarbeitung

  1. extractionthe product was extracted in ethylacetate
  2. extractionThe organic extract
  3. washwas washed in turn with diluted sodium hydroxide and water
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated under reduced pressure
  6. customThe product was crystallized from isopropyl ether

Quellen und Nachweise

ORD-Eintrag
ord-8c6dde35167a4e79a633a4157c8375f4
Quelldatensatz
uspto-grants-1978_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04122204

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