Cesium carbonate → Dimethyl-sulfamic acid 5-tert-butyl-2-methyl-4-thiocyanato-phenyl ester

HRID 1003864Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1003864
[C:1]([C:5]1[C:6]([S:13][C:14]#[N:15])=[CH:7][C:8]([CH3:12])=[C:9]([OH:11])[CH:10]=1)([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[Cs+].[Cs+].[CH3:22][N:23]([CH3:28])[S:24](Cl)(=[O:26])=[O:25]>C(#N)C>[C:1]([C:5]1[C:6]([S:13][C:14]#[N:15])=[CH:7][C:8]([CH3:12])=[C:9]([O:11][S:24](=[O:26])(=[O:25])[N:23]([CH3:28])[CH3:22])[CH:10]=1)([CH3:4])([CH3:2])[CH3:3]

Komponenten

5

Edukt 3

HCID 10796Cesium carbonateHCID 83372Dimethylsulphamoyl chlorideHCID 105609555-tert-Butyl-2-methyl-4-thiocyanato-phenol

Produkt 1

HCID 10496539Dimethyl-sulfamic acid 5-tert-butyl-2-methyl-4-thiocyanato-phenyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

To a round bottom flask equipped with a condenser and magnetic stirrer were added 5-tert-butyl-2-methyl-4-thiocyanato-phenol prepared in Example GGG (1.5 g, 6.8 mmol), cesium carbonate (2.44 g, 7.49 mmol), and acetonitrile (30 mL). This slurry was brought to reflux for 15 minutes. Dimethyl sulfamoyl chloride (0.80 mL, 7.49 mmol) was added to the slurry via syringe. The reaction was quenched with brine and extracted with EtOAc; the organic layer was dried (MgSO4) and concentrated. The residue was submitted to column chromatography (7:3 hexane:EtOAc) to give the title compound. 1H NMR (CDCl3) δ 1.46 (s, 9 H), 2.22 (s, 3 H), 3.03 (s, 6 H), 7.30 (s, 1 H), 7.47 (s, 1 H).

Aufarbeitung

  1. customTo a round bottom flask equipped with a condenser and magnetic stirrer
  2. temperatureto reflux for 15 minutes
  3. customThe reaction was quenched with brine
  4. extractionextracted with EtOAc
  5. dry with materialthe organic layer was dried (MgSO4)
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-4866e2dcf32a490ca41a12efdf1dd92a
Quelldatensatz
uspto-grants-2000_04
Patentnummer
US06046355

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