Toluene → Methyl-2-methoxy-5-benzthioamido-benzoate

HRID 840605ノート

反応式

HRID 840605 の反応式
[CH3:1][O:2][C:3](=[O:21])[C:4]1[CH:9]=[C:8]([NH:10][C:11](=O)[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:7]=[CH:6][C:5]=1[O:19][CH3:20].COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:31])=CC=1.C1(C)C=CC=CC=1>C(OCC)(=O)C>[CH3:1][O:2][C:3](=[O:21])[C:4]1[CH:9]=[C:8]([NH:10][C:11](=[S:31])[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:7]=[CH:6][C:5]=1[O:19][CH3:20]

参加物

5

反応物 3

HCID 1140TolueneHCID 87949Lawesson's reagentHCID 22620052Methyl-2-methoxy-5-benzamidobenzoate

生成物 1

HCID 86753484Methyl-2-methoxy-5-benzthioamido-benzoate収率 89.3%

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

実験手順

A 2 liter round bottom flask was charged with 15.7 grams (55 mmol) methyl-2-methoxy-5-benzamidobenzoate and 22.2 grams (55 mmol) of Lawesson's reagent followed by 500 mL of toluene. The reaction mixture was heated under reflux for 1.5 hours. The mixture was diluted with 500 mL of ethyl acetate, and washed with 250 mL of saturated aqueous bicarbonate solution, followed by washes with water and brine. The organic layer was dried over sodium sulfate, filtered and evaporated. The residue was chromatographed on silica eluting with 96/4 methylene chloride-ether. There was obtained 14.8 grams (89%) of desired material.

後処理

  1. temperatureThe reaction mixture was heated
  2. temperatureunder reflux for 1.5 hours
  3. washwashed with 250 mL of saturated aqueous bicarbonate solution
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was chromatographed on silica eluting with 96/4 methylene chloride-ether

出典と根拠

ORDレコード
ord-8fb6b0a3f53c4d74a52d9432e7925bc7
出典データセット
uspto-grants-2002_04
特許番号
US06369074B1

反応ノート

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