Water → 2-Amino-2-(2,3-dichlorophenyl)ethyl carbamate

HRID 220693Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 220693
[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1[CH:9]([NH:12]C(=O)OC(C)(C)C)[CH2:10][OH:11].ClS([N:24]=[C:25]=[O:26])(=O)=O.O.C(=O)([O-])O.[Na+]>C(#N)C>[C:25](=[O:26])([O:11][CH2:10][CH:9]([NH2:12])[C:3]1[CH:4]=[CH:5][CH:6]=[C:7]([Cl:8])[C:2]=1[Cl:1])[NH2:24]

Komponenten

6

Edukt 4

HCID 962WaterHCID 70918Chlorosulfonyl isocyanateHCID 516892Sodium BicarbonateHCID 59536916tert-butyl N-[1-(2,3-dichlorophenyl)-2-hydroxyethyl]carbamate

Produkt 1

HCID 595368632-Amino-2-(2,3-dichlorophenyl)ethyl carbamate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

Of the compound from Example 182A, 290 mg (about 0.95 mmol) were introduced in 5 ml of acetonitrile under argon. At −15° C., 115 μl (1.33 mmol) of chlorosulphonyl isocyanate were added dropwise. After 30 min, the reaction solution was admixed with 20 ml of water and heated at 60° C. overnight. The reaction mixture was cooled and introduced into saturated aqueous sodium hydrogen carbonate solution. It was extracted with twice 20 ml of ethyl acetate. The combined organic phases were dried over sodium sulphate, filtered and freed from the solvent on a rotary evaporator. Drying in an HV gave 176 mg (66% of theory) of the title compound in 89% purity.

Aufarbeitung

  1. temperatureThe reaction mixture was cooled
  2. extractionIt was extracted with twice 20 ml of ethyl acetate
  3. dry with materialThe combined organic phases were dried over sodium sulphate
  4. filtrationfiltered
  5. customfreed from the solvent on a rotary evaporator
  6. customDrying in an HV

Quellen und Nachweise

ORD-Eintrag
ord-f52834b62de54de6ab4ceb3680d844b1
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08202895B2

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