Benzoyl chloride → 2-Chloro-4-(3-benzoylthioureido)benzoic acid methyl ester

HRID 24719

Reaktionsgleichung

Reaktionsgleichung von HRID 24719
[C:1](SC#N)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(Cl)(=O)C1C=CC=CC=1.[S-:21][C:22]#[N:23].[NH4+].[CH3:25][O:26][C:27](=[O:36])[C:28]1[CH:33]=[CH:32][C:31]([NH2:34])=[CH:30][C:29]=1[Cl:35]>CC(C)=O.CC#N>[CH3:25][O:26][C:27](=[O:36])[C:28]1[CH:33]=[CH:32][C:31]([NH:34][C:22]([NH:23][C:1](=[O:8])[C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[S:21])=[CH:30][C:29]=1[Cl:35]

Komponenten

7

Edukt 4

HCID 7412Benzoyl chlorideHCID 15666Ammonium thiocyanateHCID 11839197Methyl 4-Amino-2-chlorobenzoateHCID 13203561Benzoyl thiocyanate

Produkt 1

HCID 542298402-Chloro-4-(3-benzoylthioureido)benzoic acid methyl ester

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 180AcetoneLösungsmittelHCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

Benzoyl thiocyanate was generated by refluxing a solution of benzoyl chloride (0.31 mL) and ammonium thiocyanate (0.20 g) in acetone (15 mL) for 30 min. To this solution was added a solution of 4-amino-2-chlorobenzoic acid methyl ester (0.5 g) in CH3CN (10 mL) and the mixture was refluxed for 5 h. The solvent was removed and the residue was partitioned between CH2Cl2 and water. The organic layer was separated, washed with brine, dried and evaporated. The residue was purified by column chromatography to yield 2-chloro-4-(3-benzoylthioureido)benzoic acid methyl ester (0.71 g). ESMS: 349 (MH+).

Aufarbeitung

  1. temperaturethe mixture was refluxed for 5 h
  2. customThe solvent was removed
  3. customthe residue was partitioned between CH2Cl2 and water
  4. customThe organic layer was separated
  5. washwashed with brine
  6. customdried
  7. customevaporated
  8. customThe residue was purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-5addadf8094e4a8f8757a7f561e58be7
Quelldatensatz
uspto-grants-2005_02
Patentnummer
US06855843B2

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