Isopropyl iodide → Methyl 3-amino-2-methyl-6-(1-methylethylsulphenyl)-benzoate

HRID 1288714

Reaktionsgleichung

Reaktionsgleichung von HRID 1288714
[NH2:1][C:2]1[C:3]([CH3:15])=[C:4]([C:9](SC#N)=[CH:10][CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].[S-2:16].[Na+].[Na+].I[CH:20]([CH3:22])[CH3:21]>C(O)C.O>[NH2:1][C:2]1[C:3]([CH3:15])=[C:4]([C:9]([S:16][CH:20]([CH3:22])[CH3:21])=[CH:10][CH:11]=1)[C:5]([O:7][CH3:8])=[O:6]

Komponenten

6

Edukt 3

HCID 6362Isopropyl iodideHCID 14804Sodium SulfideHCID 14801188Methyl 3-amino-2-methyl-6-thiocyanatobenzoate

Produkt 1

HCID 54177219Methyl 3-amino-2-methyl-6-(1-methylethylsulphenyl)-benzoateAusbeute 75,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
5 °C

Versuchsvorschrift

A suspension of methyl 3-amino-2-methyl-6-thiocyanatobenzoate (22.2 g) in ethanol was added to a solution of sodium sulphide (26.6 g) in water. The resultant mixture was stirred at room temperature for 1 hour and then cooled to 5° C. 2-Iodopropane (19.36 g) was added and the mixture was allowed to warm to room temperature and stirred for 2 hours. It was evaporated to dryness and the residue was suspended in aqueous sodium chloride solution and extracted with dichloromethane. The organic layer was dried (MgSO4) and filtered. The filtrate was evaporated to dryness to give methyl 3-amino-2-methyl-6-(1-methylethylsulphenyl)benzoate (18 g) as a yellow oil NMR(CDCl3) 1.2(d,6H) 2.0(s,3H) 3.0(m,1H) 3.8(bs,2H) 3.9(s,1H) 6.5(d,1H) 7.0(d,1H).

Aufarbeitung

  1. temperatureto warm to room temperature
  2. customIt was evaporated to dryness
  3. extractionextracted with dichloromethane
  4. dry with materialThe organic layer was dried (MgSO4)
  5. filtrationfiltered
  6. customThe filtrate was evaporated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-2facbc2a476e4873862188ab8c3c6792
Quelldatensatz
uspto-grants-1998_05
Patentnummer
US05747424

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