Potassium Hydroxide → 2,3,4,5-Tetrahydro-1,5-benzoxazepine

HRID 50980

반응식

HRID 50980 반응식
[OH-].[K+].ClC[CH2:5][CH2:6][N:7]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[O:9][C:8]1=O>C(O)CCC>[O:9]1[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[NH:7][CH2:6][CH2:5][CH2:8]1

참가 물질

4

반응물 2

HCID 14797Potassium HydroxideHCID 100360722(3H)-Benzoxazolone, 3-(3-chloropropyl)-

생성물 1

HCID 5777522,3,4,5-Tetrahydro-1,5-benzoxazepine수율 54.4%

시약·촉매·용매 1

HCID 2631-Butanol용매

실험 절차

Powdered KOH (37.60 g, 0.67 mol) was added to a slurry of 3-(3-chloropropyl)-1,3-benzoxazol-2(3H)-one (35.75 g, 0.169 mol) in n-butanol (450 mL) under N2 gas and refluxed for 52 hours. The mixture was filtered and reduced to dryness under reduced pressure. The residue was taken up in H2O (500 mL) and extracted with ether (3×200 mL). The organic was washed with 10% HCl (2×200 mL), dried over MgSO4, and stripped of solvent under reduced pressure. Purification by flash chromatography (50% EtOAc in hexanes) yielded 13.72 g (54%) of 2,3,4,5-tetrahydro-1,5-benzoxazepine as a powder, m.p. 50-51° C. (M+H)+ 149.

후처리

  1. temperaturerefluxed for 52 hours
  2. filtrationThe mixture was filtered
  3. extractionextracted with ether (3×200 mL)
  4. washThe organic was washed with 10% HCl (2×200 mL)
  5. dry with materialdried over MgSO4
  6. customPurification by flash chromatography (50% EtOAc in hexanes)

출처 및 근거

ORD 기록
ord-976260e899e04a89a7c17e9e744c8602
출처 데이터셋
uspto-grants-2004_03
특허 번호
US06713471B1

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