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

HRID 1060492

반응식

HRID 1060492 반응식
[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]

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 180Acetone용매HCID 6342Acetonitrile용매

실험 절차

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+).

후처리

  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

출처 및 근거

ORD 기록
ord-ccfd7fc569024970b6b5c3dec57dc888
출처 데이터셋
uspto-grants-2003_02
특허 번호
US06521666B1

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