Reaktion #52186

ord-2a1b0aad832c47bf93263209157fb435

Reaktionsgleichung

COS(=O)(=O)OC
dimethyl sulphate
CNc1ccc(C(=O)O)cc1[N+](=O)[O-]
4-methylamino-3-nitro-benzoic acid
O=C([O-])[O-].[K+].[K+]
K2CO3
→
CNc1c(C(=O)OC)cccc1[N+](=O)[O-]
Methylamino-3-nitro-benzoic acid-methyl ester

Edukte

COS(=O)(=O)OC
dimethyl sulphate
CNc1ccc(C(=O)O)cc1[N+](=O)[O-]
4-methylamino-3-nitro-benzoic acid
O=C([O-])[O-].[K+].[K+]
K2CO3

Reagenzien

Keine

Lösungsmittel

O
water
CN(C)C=O
dimethyl formamide

Reaktionsbedingungen

Temperatur
60°CELSIUS
Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    workup.STIRRINGIt is stirred for 15 minutes
  2. 2
    TemperaturAfter cooling
  3. 3
    Filtrationthe precipitated solids are filtered off
  4. 4
    Waschenwashed with water
  5. 5
    Sonstigedried

Vorschrift

9.8 g (50 mmol) of 4-methylamino-3-nitro-benzoic acid are treated in 50 ml of dimethyl formamide (DMF) with K2CO3 (14 g). 5 ml of dimethyl sulphate are added dropwise to this mixture over 10 minutes with stirring. It is stirred for 15 minutes and heated for 0.5 hours at 60° C. After cooling, it is diluted with water, the precipitated solids are filtered off, washed with water and dried. Yield: 9.8 g (93%); M.Pt.: 138-140° C.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US06855713B2uspto-grants-2005_02