Dimethyl Sulfate → HCID 22364788, Verbindung

HRID 1781636Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1781636
[Cl:1][C:2]1[CH:3]=[C:4]([NH2:14])[C:5](=[C:9]([N+:11]([O-:13])=[O:12])[CH:10]=1)[C:6]([OH:8])=[O:7].[OH-].[CH2:16]([N+](CCCC)(CCCC)CCCC)CCC.S(OC)(OC)(=O)=O>ClCCl>[CH3:16][O:7][C:6](=[O:8])[C:5]1[C:4](=[CH:3][C:2]([Cl:1])=[CH:10][C:9]=1[N+:11]([O-:13])=[O:12])[NH2:14]

Komponenten

5

Edukt 3

HCID 6497Dimethyl SulfateHCID 2723671Tetrabutylammonium HydroxideHCID 190467352-Amino-4-chloro-6-nitrobenzoic acid

Produkt 1

HCID 22364788HCID 22364788, VerbindungAusbeute 48,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

3.25 g (15 mmol) of 4-chloro-6-nitro-anthranilic acid and 9.73 ml of a 40% aqueous solution of tetrabutylammonium hydroxide are placed in 65 ml of dichloromethane. Then 1.43 ml (15 mmol) of dimethyl sulfate are added dropwise thereto and the mixture is stirred for 1 hour at room temperature and washed in succession with a small amount of water and saturated sodium chloride solution. The aqueous phases are extracted by shaking with dichloromethane and the combined organic phases are dried over sodium sulfate, filtered and concentrated. The residue is stirred with a small amount of ethyl acetate. The product is precipitated with hexane and dried. 1.67 g (48.3% of theory) of 4-chloro-6-nitro-anthranilic acid methyl ester having a melting point of 114°-116° are obtained.

Aufarbeitung

  1. washwashed in succession with a small amount of water and saturated sodium chloride solution
  2. extractionThe aqueous phases are extracted
  3. stirringby shaking with dichloromethane
  4. dry with materialthe combined organic phases are dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. stirringThe residue is stirred with a small amount of ethyl acetate
  8. customThe product is precipitated with hexane
  9. customdried

Quellen und Nachweise

ORD-Eintrag
ord-d7c0badf483346398413ee261ac19298
Quelldatensatz
uspto-grants-1997_05
Patentnummer
US05633379

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