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

HRID 1060492

Reaktionsgleichung

Reaktionsgleichung von HRID 1060492
[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-ccfd7fc569024970b6b5c3dec57dc888
Quelldatensatz
uspto-grants-2003_02
Patentnummer
US06521666B1

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