Sodium Sulfite → 7-bromo-5-phenyl-2,3-dihydro-1H-1,4-benzodiazepine

HRID 1365073노트

반응식

HRID 1365073 반응식
[C:1]1([C:7]2[C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=3[NH:11][CH2:10][CH2:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br:18]N1C(=O)CCC1=O.S([O-])([O-])=O.[Na+].[Na+]>O1CCCC1>[Br:18][C:15]1[CH:16]=[CH:17][C:12]2[NH:11][CH2:10][CH2:9][N:8]=[C:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[C:13]=2[CH:14]=1

참가 물질

5

반응물 3

HCID 24437Sodium SulfiteHCID 67184N-bromobutanimideHCID 123369265-phenyl-2,3-dihydro-1H-1,4-benzodiazepine

생성물 1

HCID 215088487-bromo-5-phenyl-2,3-dihydro-1H-1,4-benzodiazepine

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

A round-bottomed flask was charged with 5-phenyl-2,3-dihydro-1H-1,4-benzodiazepine (1.0 g) and tetrahydrofuran. The mixture was treated with N-bromosuccinimide (1.1 equiv.) then stirred at room temperature for 15 min. The reaction was then treated with an excess of sodium sulfite and the mixture was concentrated to dryness. The residue was dissolved in water and then extracted with ethyl acetate. The organic extracts were dried over magnesium sulfate, filtered and concentrated to an oil. Solids were induced from a methylene chloride/diethyl ether mixture and collected on filter. The solids were washed with diethyl ether then air-dried to provide 7-bromo-5-phenyl-2,3-dihydro-1H-1,4-benzodiazepine (0.60 g). H1 NMR (d6-dmso): 7.38-7.44 (m, 5H), 7.26 (dd, 1H), 6.86 (d, 1H), 6.75 (d, 1H), 6.41 (br t, 1H), 3.89 (m, 2H), 3.55 (m, 2H).

후처리

  1. concentrationthe mixture was concentrated to dryness
  2. dissolutionThe residue was dissolved in water
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic extracts were dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated to an oil
  7. customcollected
  8. filtrationon filter
  9. washThe solids were washed with diethyl ether
  10. customthen air-dried

출처 및 근거

ORD 기록
ord-b5b0861a52744a6d8d5bce35ceef68f5
출처 데이터셋
uspto-grants-2011_02
특허 번호
US07888503B2

반응 노트

불러오는 중…