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

HRID 24719

反応式

HRID 24719 の反応式
[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]

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 180Acetone溶媒HCID 6342Acetonitrile溶媒

実験手順

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+).

後処理

  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

出典と根拠

ORDレコード
ord-5addadf8094e4a8f8757a7f561e58be7
出典データセット
uspto-grants-2005_02
特許番号
US06855843B2

関連ノート

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