Dimethyl Sulfide → N-isopropyl-2-(methylamino)-5-phenoxybenzamide

HRID 2099978

Reaktionsgleichung

Reaktionsgleichung von HRID 2099978
[CH:1]([NH:3][C:4]1[CH:15]=[CH:14][C:13]([O:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:12][C:5]=1[C:6]([NH:8][CH:9]([CH3:11])[CH3:10])=[O:7])=O.S(C)C>C1COCC1>[CH:9]([NH:8][C:6](=[O:7])[C:5]1[CH:12]=[C:13]([O:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:14]=[CH:15][C:4]=1[NH:3][CH3:1])([CH3:11])[CH3:10]

Komponenten

4

Edukt 2

HCID 1068Dimethyl SulfideHCID 577968922-formamido-N-isopropyl-5-phenoxybenzamide

Produkt 1

HCID 57796896N-isopropyl-2-(methylamino)-5-phenoxybenzamideAusbeute 29,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

A solution of 44A (55 mg, 0.19 mmol) in THF (1 mL) at 0° C. was treated with BH3.SMe2 (0.09 mL, 0.93 mmol). The resulting yellow solution was warmed to 50° C. for 1 hour, and then cooled to 0° C. and quenched with MeOH (0.25 mL). The resulting solution was treated with acetic acid (0.1 mL) and warmed to 50° C. for 6 hours. The solution was concentrated to dryness and purified by chromatography (SiO2, 10% MeOH in CHCl3) to afford 44B (16 mg).

Aufarbeitung

  1. temperaturecooled to 0° C.
  2. customquenched with MeOH (0.25 mL)
  3. additionThe resulting solution was treated with acetic acid (0.1 mL)
  4. temperaturewarmed to 50° C. for 6 hours
  5. concentrationThe solution was concentrated to dryness
  6. custompurified by chromatography (SiO2, 10% MeOH in CHCl3)

Quellen und Nachweise

ORD-Eintrag
ord-53fbd5f1ae7b4862a962e7e8ac3f4c7e
Quelldatensatz
uspto-grants-2009_08
Patentnummer
US07569725B2

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