Benzaldehyde → Benzylidene-(3-bromo-1-propylamine)

HRID 555331ノート

反応式

HRID 555331 の反応式
[Br:1][CH2:2][CH2:3][CH2:4][NH2:5].C(N(CC)CC)C.[CH:13](=O)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.S([O-])([O-])(=O)=O.[Mg+2]>C(Cl)(Cl)Cl>[CH:13](=[N:5][CH2:4][CH2:3][CH2:2][Br:1])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

参加物

6

反応物 4

HCID 240BenzaldehydeHCID 8471TriethylamineHCID 24083Sulfuric acid magnesium salt (1:1)HCID 787023-Bromopropylamine

生成物 1

HCID 11053338Benzylidene-(3-bromo-1-propylamine)収率 100%

試薬・触媒・溶媒 1

HCID 6212Chloroform溶媒

実験手順

The hydrobromide salt of 3-bromopropylamine (5.364 g, 24.50 mmol) was treated with triethylamine (4 mL) in CHCl3 (100 mL) and allowed to stir at room temperature for 5 min. Benzaldehyde (2.000 g, 18.85 mmol) and magnesium sulfate (6.000 g) were added and the reaction mixture was allowed to stir at room temperature for 16 h. The reaction mixture was filtered and the filter pad was washed with CHCl3 (50 mL). The filtrate was washed with water (3×50 mL), sat NaCl (50 mL), dried over sodium sulfate, and concentrated to provide a yellow oil (4.262 g, 100%). IR (film) 1645, 754, and 693 cm−1; 1H NMR (CDCl3) δ 8.34 (s, 1 H), 7.76 (m, 2 H), 7.44 (m, 3 H), 3.78 (dt, J=6.3 Hz and 1.3 Hz, 2 H), 3.52 (t, J=6.5 Hz, 2 H), 2.31 (pent, J=6.4 Hz, 2 H); ESIMS m/z (rel intensity) 226/228 (MH+, 100/91). Anal. (C10H12BrN) C, H, N.

後処理

  1. stirringto stir at room temperature for 16 h
  2. filtrationThe reaction mixture was filtered
  3. washthe filter pad was washed with CHCl3 (50 mL)
  4. washThe filtrate was washed with water (3×50 mL)
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated

出典と根拠

ORDレコード
ord-435a8c90322a4f258b73afa2dc933d4b
出典データセット
uspto-grants-2011_11
特許番号
US08053443B2

反応ノート

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