Dibutyltin oxide → HCID 178496911, 화합물

HRID 1388045노트

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HRID 1388045 반응식
[C:1]([C:3]1[CH:4]=[CH:5][C:6]2[O:12][CH2:11][CH2:10][C:9]([C:13]([O:15][CH3:16])=[O:14])=[CH:8][C:7]=2[CH:17]=1)#[N:2].C[Si]([N:22]=[N+:23]=[N-:24])(C)C.C([Sn](=O)CCCC)CCC>C1(C)C=CC=CC=1>[NH:22]1[C:1]([C:3]2[CH:4]=[CH:5][C:6]3[O:12][CH2:11][CH2:10][C:9]([C:13]([O:15][CH3:16])=[O:14])=[CH:8][C:7]=3[CH:17]=2)=[N:2][N:24]=[N:23]1

참가 물질

5

반응물 3

HCID 61221Dibutyltin oxideHCID 78378AzidotrimethylsilaneHCID 18472647Methyl 7-cyano-2,3-dihydro-1-benzoxepine-4-carboxylate

생성물 1

HCID 178496911HCID 178496911, 화합물수율 87%

시약·촉매·용매 1

HCID 1140Toluene용매

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온도
100 °C

실험 절차

In toluene (15 ml) was suspended methyl 7-cyano-2,3-dihydro-1-benzoxepine-4-carboxylate (642 mg, 2.80 mmol), and to the mixture were added trimethylsilyl-azide (0.929 ml, 7.00 mmol) and dibutyl tin oxide (70 mg, 0.28 mmol). The mixture was stirred at 100° C. for 24 hours and concentrated under reduced pressure. To the residue was added methanol, and the mixture was concentrated under reduced pressure. To the residue was added ethyl acetate, and the mixture was extracted with saturated sodium bicarbonate solution (30 ml, 10 ml×2). To the aqueous layer was added 6N hydrochloric acid to make the solution about pH 1, and the mixture was extracted with ethyl acetate and THF ((30 ml150 ml) and (10 ml/10 ml)×2). The organic layer was dried with anhydrous magnesium sulfate and concentrated under reduced pressure, to the residue was added ethyl acetate. Insoluble materials were filtered, which were washed with ethyl acetate and dried under reduced pressure to give methyl 7-(1H-tetrazol-5-yl)-2,3-dihydro-1-benzoxepine-4-carboxylate (662 mg, 2.43 mmol, 87%).

후처리

  1. concentrationconcentrated under reduced pressure
  2. additionTo the residue was added methanol
  3. concentrationthe mixture was concentrated under reduced pressure
  4. additionTo the residue was added ethyl acetate
  5. extractionthe mixture was extracted with saturated sodium bicarbonate solution (30 ml, 10 ml×2)
  6. additionTo the aqueous layer was added 6N hydrochloric acid
  7. extractionthe mixture was extracted with ethyl acetate and THF ((30 ml150 ml) and (10 ml/10 ml)×2)
  8. dry with materialThe organic layer was dried with anhydrous magnesium sulfate
  9. concentrationconcentrated under reduced pressure, to the residue
  10. additionwas added ethyl acetate
  11. filtrationInsoluble materials were filtered
  12. washwhich were washed with ethyl acetate
  13. customdried under reduced pressure

출처 및 근거

ORD 기록
ord-b6a533ca139e48478a2846122510665c
출처 데이터셋
uspto-grants-2001_07
특허 번호
US06268354B1

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