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

HRID 840605노트

반응식

HRID 840605 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

HCID 86753484Methyl-2-methoxy-5-benzthioamido-benzoate수율 89.3%

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-8fb6b0a3f53c4d74a52d9432e7925bc7
출처 데이터셋
uspto-grants-2002_04
특허 번호
US06369074B1

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