Dichloromethane → 4-Phenylbutanethioamide

HRID 1378604Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1378604
[C:1]1([CH2:7][CH2:8][CH2:9][C:10]([NH2:12])=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:22])=CC=1.CCCCCC.C(Cl)Cl>C1(C)C=CC=CC=1.C(O)(=O)C>[C:1]1([CH2:7][CH2:8][CH2:9][C:10]([NH2:12])=[S:22])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Komponenten

7

Edukt 4

HCID 6344DichloromethaneHCID 8058HexaneHCID 87949Lawesson's reagentHCID 2633634-Phenylbutyramide

Produkt 1

HCID 222823784-PhenylbutanethioamideAusbeute 90 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidLösungsmittelHCID 1140TolueneLösungsmittel

Versuchsvorschrift

To a solution of 4-phenylbutyramide (0.373 g, 2.28 mmol) in toluene (15 mL) was added Lawesson's reagent (0.461 g, 1.14 mmol). The reaction was refluxed overnight, cooled to room temperature and concentrated yielding an orange oil. Flash chromatography of this oil (1:1 hexane:methylene chloride with 1% acetic acid) yielded 4-phenylthiobutyramide (0.184 g) as a white solid: 1HNMR (DMSO d6 ) 400 mHz 9.33 (s, 1 H), 9.13 (s, 1 H), 7.29-7.23 (m, 2 H), 7.20-7.15 (m, 3 H), 2.56 (t, J=7.58 Hz, 2 H), 2.50-2.42 (m, 2 H), 2.00-1.85 (m, 2 H).

Aufarbeitung

  1. temperatureThe reaction was refluxed overnight
  2. concentrationconcentrated
  3. customyielding an orange oil

Quellen und Nachweise

ORD-Eintrag
ord-e3ca98cc7da242a19e85566293cd2f8e
Quelldatensatz
uspto-grants-1997_09
Patentnummer
US05668161

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