Triethylamine → (3-Trifluoromethylphenyl)thiocarbamic acid O-(4-hydroxymethyl-5-oxo-2,3,4,5-tetrahydrobenzo[b]thiepin-4-ylmethyl)ester

HRID 2265825

Reaktionsgleichung

Reaktionsgleichung von HRID 2265825
[OH:1][CH2:2][C:3]1([CH2:15][OH:16])[CH2:9][CH2:8][S:7][C:6]2[CH:10]=[CH:11][CH:12]=[CH:13][C:5]=2[C:4]1=[O:14].C(N(CC)CC)C.[F:24][C:25]([F:36])([F:35])[C:26]1[CH:27]=[C:28]([N:32]=[C:33]=[S:34])[CH:29]=[CH:30][CH:31]=1>O1CCCC1>[OH:16][CH2:15][C:3]1([CH2:2][O:1][C:33](=[S:34])[NH:32][C:28]2[CH:29]=[CH:30][CH:31]=[C:26]([C:25]([F:24])([F:35])[F:36])[CH:27]=2)[CH2:9][CH2:8][S:7][C:6]2[CH:10]=[CH:11][CH:12]=[CH:13][C:5]=2[C:4]1=[O:14]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 1372321-Isothiocyanato-3-(trifluoromethyl)benzeneHCID 670733654,4-bis(hydroxymethyl)-3,4-dihydro-2H-benzo[b]thiepin-5-one

Produkt 1

HCID 86633682(3-Trifluoromethylphenyl)thiocarbamic acid O-(4-hydroxymethyl-5-oxo-2,3,4,5-tetrahydrobenzo[b]thiepin-4-ylmethyl)ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 4,4-bis(hydroxymethyl)-3,4-dihydro-2H-benzo[b]thiepin-5-one (555 mg, 2.33 mmol) in 29 ml of tetrahydrofuran were added, at room temperature, triethylamine (0.35 ml, 2.56 mmol) and 3-(trifluoromethyl)phenyl isothiocyanate (885 μl, 5.82 mmol). The mixture was heated to reflux for 72 hours, concentrated and purified by column chromatography on silica gel (eluent: 1:2 ethyl acetate/hexane). The product was obtained in a yield of 320 mg (31%).

Aufarbeitung

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 72 hours
  3. concentrationconcentrated
  4. custompurified by column chromatography on silica gel (eluent: 1:2 ethyl acetate/hexane)
  5. customThe product was obtained in a yield of 320 mg (31%)

Quellen und Nachweise

ORD-Eintrag
ord-a1e199664d9f435fa3086fcdfb25aa66
Quelldatensatz
uspto-grants-2010_12
Patentnummer
US07858613B2

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