1-Bromooctane → N1,N1,N5,N5-tetraoctylnaphthalene-1,5-diamine

HRID 1897379

反応式

HRID 1897379 の反応式
[C:1]1([NH2:12])[C:10]2[CH:9]=[CH:8][CH:7]=[C:6]([NH2:11])[C:5]=2[CH:4]=[CH:3][CH:2]=1.Br[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21].C(=O)([O-])[O-].[K+].[K+]>C(O)CCC.[I-].[K+]>[CH2:14]([N:12]([CH2:9][CH2:10][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH3:6])[C:1]1[C:10]2[CH:9]=[CH:8][CH:7]=[C:6]([N:11]([CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[C:5]=2[CH:4]=[CH:3][CH:2]=1)[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21]

参加物

6

反応物 3

HCID 81401-BromooctaneHCID 11430Potassium CarbonateHCID 167201,5-Diaminonaphthalene

生成物 1

HCID 68441382N1,N1,N5,N5-tetraoctylnaphthalene-1,5-diamine収率 38.3%

試薬・触媒・溶媒 2

HCID 4875Potassium Iodide触媒HCID 2631-Butanol溶媒

反応条件

温度
110 °C

実験手順

Naphthalene-1,5-diamine (3.14 g, 19.8 mmol), 1-bromooctane (25.25 g, 0.130 mol), potassium carbonate (11.79 g, 85.3 mmol), and potassium iodide (0.05 g, 0.30 mmol) was stirred in dry butanol (150 ml) and heated to 110° C. for 36 h. The reaction was quenched with water and extracted with ether three times. The combined organic phase was washed three times with water and evaporated to give black oil which was distilled under reduced pressure at 90° C. to yield a black tar. This was purified with flash chromatography using hexane as mobile phase to obtain colourless oil which crystallised to yield N1,N1,N5,N5-tetraoctylnaphthalene-1,5-diamine (2.3 g, 3.79 mmol) as white crystals. 1H-NMR (CDCl3, δ): 0.85 (t, 12H), 1.0-1.4 (m, 40H), 1.4-1.6 (m, 8H), 3.08 (t, 8H), 7.1 (d, 2H), 7.35 (t, 2H), 8.01 (d, 2H) MS MALDI-TOF (m/z): 606.574

後処理

  1. customThe reaction was quenched with water
  2. extractionextracted with ether three times
  3. washThe combined organic phase was washed three times with water
  4. customevaporated
  5. customto give black oil which
  6. distillationwas distilled under reduced pressure at 90° C.
  7. customto yield a black tar
  8. customThis was purified with flash chromatography
  9. customto obtain colourless oil which
  10. customcrystallised

出典と根拠

ORDレコード
ord-cc4cbe8c62b2426983183ff61b6f89b8
出典データセット
uspto-grants-2013_08
特許番号
US08519037B2

関連ノート

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