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N-bromobutanimide → HCID 67188040, 화합물

HRID 885995
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HRID 885995 반응식
[CH3:1][C:2]1([CH3:24])[NH:7][C:6](=[O:8])[C:5]2[S:9][C:10]([N:12]3[C:17]4[CH:18]=[CH:19][C:20]([O:22][CH3:23])=[CH:21][C:16]=4[O:15][CH2:14][CH2:13]3)=[N:11][C:4]=2[CH2:3]1.[Br:25]N1C(=O)CCC1=O>CC#N.C1COCC1>[Br:25][C:19]1[C:20]([O:22][CH3:23])=[CH:21][C:16]2[O:15][CH2:14][CH2:13][N:12]([C:10]3[S:9][C:5]4[C:6](=[O:8])[NH:7][C:2]([CH3:24])([CH3:1])[CH2:3][C:4]=4[N:11]=3)[C:17]=2[CH:18]=1
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참가 물질

5

반응물 2

HCID 67184N-bromobutanimideHCID 44577952HCID 44577952, 화합물

생성물 1

HCID 67188040HCID 67188040, 화합물수율 100.8%

시약·촉매·용매 2

HCID 6342Acetonitrile용매HCID 8028Tetrahydrofuran용매

실험 절차

To a stirred solution of Example 489 (0.05 g, 0.145 mmol) in MeCN (1 mL) and THF (1 mL) was added N-bromosuccinimide (0.026 g, 0.145 mmol). The mixture was stirred at r.t. overnight and then concentrated in vacuo. EtOAc (10 mL) and 1% aqueous sodium sulfite (5 mL) were added and the mixture was rapidly stirred for 10 minutes. The aqueous layer was extracted with EtOAc (10 mL) and then DCM (2×10 mL). The EtOAc extracts were concentrated in vacuo and the residue was dissolved in DCM (5 mL). The combined organic fractions were washed with brine (10 mL), dried (MgSO4), filtered and the solvent was evaporated in vacuo to give the title compound (0.062 g, 100%) as a light brown solid. δH (CDCl3) 8.17 (1H, s), 6.52 (1H, s), 5.22 (1H, s), 4.35-4.30 (2H, m), 4.10-4.05 (2H, m), 3.86 (3H, s), 2.88 (2H, s), 1.39 (6H, s). LCMS (ES+) 424.1, 426.0 (M+H)+, RT 3.47 minutes (Method 1).

후처리

  1. concentrationconcentrated in vacuo
  2. additionEtOAc (10 mL) and 1% aqueous sodium sulfite (5 mL) were added
  3. stirringthe mixture was rapidly stirred for 10 minutes
  4. extractionThe aqueous layer was extracted with EtOAc (10 mL)
  5. concentrationThe EtOAc extracts were concentrated in vacuo
  6. dissolutionthe residue was dissolved in DCM (5 mL)
  7. washThe combined organic fractions were washed with brine (10 mL)
  8. dry with materialdried (MgSO4)
  9. filtrationfiltered
  10. customthe solvent was evaporated in vacuo

출처 및 근거

ORD 기록
ord-405b584162444944a94f7c65c1e2c204
출처 데이터셋
uspto-grants-2012_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08242116B2

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