Allyl isocyanate → N-(2-Propenyl)-3-[4-(trifluoromethyl)phenoxy]-1-azetidinecarboxamide

HRID 974555

반응식

HRID 974555 반응식
[F:1][C:2]([F:15])([F:14])[C:3]1[CH:13]=[CH:12][C:6]([O:7][CH:8]2[CH2:11][NH:10][CH2:9]2)=[CH:5][CH:4]=1.[CH2:16]([N:19]=[C:20]=[O:21])[CH:17]=[CH2:18]>C(OC(C)C)(C)C>[CH2:16]([NH:19][C:20]([N:10]1[CH2:9][CH:8]([O:7][C:6]2[CH:5]=[CH:4][C:3]([C:2]([F:1])([F:14])[F:15])=[CH:13][CH:12]=2)[CH2:11]1)=[O:21])[CH:17]=[CH2:18]

참가 물질

4

반응물 2

HCID 15123Allyl isocyanateHCID 128124993-[4-(Trifluoromethyl)phenoxy]azetidine

생성물 1

HCID 15053419N-(2-Propenyl)-3-[4-(trifluoromethyl)phenoxy]-1-azetidinecarboxamide

시약·촉매·용매 1

HCID 7914Diisopropyl Ether용매

실험 절차

A solution of 8.7 g (0.04 mole) of crude 3-[4-(trifluoromethyl)phenoxy]azetidine in 75 ml of isopropyl ether was stirred under a blanket of nitrogen while 4.2 g (0.05 mole) of 2-propenyl isocyanate was added dropwise. After stirring for 3 days, no crystalline product precipitated. The reaction mixture was concentrated to a dark reddish oil. TLC (20% ethyl acetate/methylene chloride on silica gel) showed at least 6 spots, all well separated. The residue was dissolved in chloroform, chromatographed on a 350 g silica gel column and eluted with chloroform until the reddish forerun was removed. The column was then eluted with an ethyl acetate/chloroform gradient to 4% ethyl acetate. All the fractions were combined and concentrated to give 4.8 of orange oil, which crystallized on standing. Recrystallization from acetone/cyclohexane gave 3.3 g (27.5%) of being crystals, m.p. 91°-92.5° C.

후처리

  1. additionwas added dropwise
  2. customno crystalline product precipitated
  3. concentrationThe reaction mixture was concentrated to a dark reddish oil
  4. customall well separated
  5. dissolutionThe residue was dissolved in chloroform
  6. customchromatographed on a 350 g silica gel column
  7. washeluted with chloroform until the reddish forerun
  8. customwas removed
  9. washThe column was then eluted with an ethyl acetate/chloroform gradient to 4% ethyl acetate
  10. concentrationconcentrated
  11. customto give 4.8 of orange oil, which
  12. customcrystallized
  13. customRecrystallization from acetone/cyclohexane
  14. customgave 3.3 g (27.5%)

출처 및 근거

ORD 기록
ord-2d60b1d155fa44878f040481b455c353
출처 데이터셋
uspto-grants-1991_11
특허 번호
US05068231

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