Water → HCID 11965692, Verbindung

HRID 1441530Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1441530
[CH3:1][O:2][C:3](=[O:21])[C:4]1[CH:9]=[C:8]([C:10](=[O:12])[CH3:11])[C:7]([C:13]([F:16])([F:15])[F:14])=[CH:6][C:5]=1[NH:17]C(=O)C.O.S(=O)(=O)(O)O>CO.CCOC(C)=O>[CH3:1][O:2][C:3](=[O:21])[C:4]1[CH:9]=[C:8]([C:10](=[O:12])[CH3:11])[C:7]([C:13]([F:14])([F:16])[F:15])=[CH:6][C:5]=1[NH2:17]

Komponenten

6

Edukt 3

HCID 962WaterHCID 1118Sulfuric AcidHCID 591644065-Acetyl-2-acetylamino-4-trifluoromethyl-benzoic acid methyl ester

Produkt 1

HCID 11965692HCID 11965692, VerbindungAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A solution of 5-acetyl-2-acetylamino-4-trifluoromethyl-benzoic acid methyl ester (11.5 g, 37.8 mmol) in MeOH (120 mL)/water (24 mL) was cooled to 0° C. and concentrated sulfuric acid (15.0 mL, 271 mmol) was added dropwise. Upon completion of the addition, the mixture was heated to reflux for 45 min under nitrogen, and then allowed to cool to r.t. The mixture was diluted with EtOAc and washed once with water. The organic layer was dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo providing 5-acetyl-2-amino-4-trifluoromethyl-benzoic acid methyl ester (9.87 g, 37.8 mmol, quantitative) as a white solid, m.p. 118-121° C., ESI-MS: m/z 262 [M+H]+.

Aufarbeitung

  1. additionUpon completion of the addition
  2. temperaturethe mixture was heated
  3. temperatureto reflux for 45 min under nitrogen
  4. washwashed once with water
  5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-0bd8ccc6f8e646c3a99760f41f36008d
Quelldatensatz
uspto-grants-2010_02
Patentnummer
US07655666B2

Notizen zur Reaktion

Wird geladen…