Sulfuric Acid → N-[2-(3-bromophenyl)-1,1-dimethylethyl]-2-chloroacetamide

HRID 494419Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 494419
[Cl:1][CH2:2][C:3]#[N:4].[Br:5][C:6]1[CH:7]=[C:8]([CH2:12][C:13]([CH3:16])(O)[CH3:14])[CH:9]=[CH:10][CH:11]=1.S(=O)(=O)(O)[OH:18].C(=O)([O-])[O-].[K+].[K+]>C(O)(=O)C>[Br:5][C:6]1[CH:7]=[C:8]([CH2:12][C:13]([NH:4][C:3](=[O:18])[CH2:2][Cl:1])([CH3:14])[CH3:16])[CH:9]=[CH:10][CH:11]=1

Komponenten

6

Edukt 4

HCID 1118Sulfuric AcidHCID 7856ChloroacetonitrileHCID 11430Potassium CarbonateHCID 230877121-(3-Bromophenyl)-2-methylpropan-2-ol

Produkt 1

HCID 58907445N-[2-(3-bromophenyl)-1,1-dimethylethyl]-2-chloroacetamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Chloroacetonitrile (6.63 mL, 105 mmol) was added to a stirred solution of 1-(3-bromophenyl)-2-methylpropan-2-ol) (Preparation 16) (12.0 g, 52.0 mmol) in acetic acid (25 mL) at room temperature. The resulting solution was cooled to 0° C. and concentrated sulfuric acid (25 mL) was added keeping the temperature <10° C. The resulting solution was left to stir for 1 hour and then poured onto ice and basified by the addition of solid potassium carbonate. The product was extracted with ethyl acetate (2×500 mL), the organics combined and washed with water (50 mL), dried (sodium sulfate) and the solvent removed in vacuo to afford the title compound as an orange solid (16.08 g).

Aufarbeitung

  1. customthe temperature <10° C
  2. waitThe resulting solution was left
  3. additionpoured onto ice
  4. extractionThe product was extracted with ethyl acetate (2×500 mL)
  5. washwashed with water (50 mL)
  6. dry with materialdried (sodium sulfate)
  7. customthe solvent removed in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-84580ab7ebda4c3387f9ce01ac892c09
Quelldatensatz
uspto-grants-2009_05
Patentnummer
US07538141B2

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