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

HRID 1365073ノート

反応式

HRID 1365073 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-b5b0861a52744a6d8d5bce35ceef68f5
出典データセット
uspto-grants-2011_02
特許番号
US07888503B2

反応ノート

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