Lawesson's reagent → 7-bromo-4,5-dihydrospiro[benzo[b][1,4]diazepine-3,1'-cyclopropane]-2(1H)-thione

HRID 1485430노트

반응식

HRID 1485430 반응식
[Br:1][C:2]1[CH:15]=[CH:14][C:5]2[NH:6][C:7](=O)[C:8]3([CH2:11][NH:12][C:4]=2[CH:3]=1)[CH2:10][CH2:9]3.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:25])=CC=1>O1CCCC1>[Br:1][C:2]1[CH:15]=[CH:14][C:5]2[NH:6][C:7](=[S:25])[C:8]3([CH2:11][NH:12][C:4]=2[CH:3]=1)[CH2:10][CH2:9]3

참가 물질

4

반응물 2

HCID 87949Lawesson's reagentHCID 709789007-bromo-4,5-dihydrospiro[benzo[b][1,4]diazepine-3,1'-cyclopropan]-2(1H)-one

생성물 1

HCID 867185037-bromo-4,5-dihydrospiro[benzo[b][1,4]diazepine-3,1'-cyclopropane]-2(1H)-thione수율 44.1%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

A solution of 7-bromo-4,5-dihydrospiro[benzo[b][1,4]diazepine-3,1′-cyclopropan]-2(1H)-one (267 mg, 1.0 mmol) and Lawesson's reagent (606 mg, 1.5 mmol) in tetrahydrofuran (15 mL) was heated to 80° C., and maintained at the same temperature for 1 hours. The mixture was concentrated. To the residue was added water (50 mL), extracted with ethyl acetate (50 mL). The organic phase was washed with water (50 mL*2), dried by sodium sulfate, filtered and concentrated to give a residue. The residue was purified by column chromatography (silica gel, petroleum ether/ethyl acetate=6:1) to afford 7-bromo-4,5-dihydrospiro[benzo[b][1,4]diazepine-3,1′-cyclopropane]-2(1H)-thione (125 mg, 44%).

후처리

  1. temperaturemaintained at the same temperature for 1 hours
  2. concentrationThe mixture was concentrated
  3. additionTo the residue was added water (50 mL)
  4. extractionextracted with ethyl acetate (50 mL)
  5. washThe organic phase was washed with water (50 mL*2)
  6. dry with materialdried by sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customto give a residue
  10. customThe residue was purified by column chromatography (silica gel, petroleum ether/ethyl acetate=6:1)

출처 및 근거

ORD 기록
ord-d62d78ea428c41fe80dacecc2a5d6beb
출처 데이터셋
uspto-grants-2016_08
특허 번호
US09422292B2

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