Methanol → 3-(9-Phenylxanthen-9-yl)aminopropyne

HRID 849439ノート

反応式

HRID 849439 の反応式
Cl[C:2]1([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:15]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[O:9][C:8]2[C:3]1=[CH:4][CH:5]=[CH:6][CH:7]=2.[NH2:22][CH2:23][C:24]#[CH:25].CO>CN(C=O)C>[C:16]1([C:2]2([NH:22][CH2:23][C:24]#[CH:25])[C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][C:8]=3[O:9][C:10]3[C:15]2=[CH:14][CH:13]=[CH:12][CH:11]=3)[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

参加物

5

反応物 3

HCID 887MethanolHCID 1706559-Chloro-9-phenyl-9H-xantheneHCID 239041Propargylamine

生成物 1

HCID 100867933-(9-Phenylxanthen-9-yl)aminopropyne収率 82%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

9-Chloro-9-phenylxanthen (14.7 g, 50 mmol) was added in two equal portions over 0.5 h to a stirred solution of 3-aminopropyne (8.6 mL, 125 mmol) in DMF (100 mL). After 3 h, MeOH (20 mL) was added and the reaction mixture was stirred for 15 min. The mixture was then extracted into diethyl ether (500 mL) and washed with H2O (3×300 mL), dried (Na2SO4), and the solvent removed under vacuum. The resulting yellow oil was dried under high vacuum (4 h), and then redissolved in hot diethyl ether (70 mL). The solution was kept at -20° C. for 24 h and then filtered, the solid washed with ice-cold hexand (2×50 mL) followed by ice-cold diethyl ether (2×50 mL), giving 12 as a colourless powder (12.7 g, 82%), mp 116-8° C. 1H NMR (d6 -DMSO): δ2.86 (dd, 2H, H3, J=7.3, 4.4 Hz), 2.99 (t, 1H, H1, J=2.4 Hz), 4.01 (t, 1H, NH, J=7.2 Hz), 6.98-7.50 (m, 13H, Px CH). 13C NMR (d6 -DMSO): δ32.8 (C3), 59.7 (Px C9), 73.4 (C1), 82.7 (C2), 1160.0 and 123.5 (Px CH), 125.0 (Px C8a and C9a), 126.3, 126.4, 128.0, 128.6, 128.7 (Px CH), 149.5 (Px C1'), 150.7 (Px C4a and C10a). FABMS m/z 311 (M+). Anal. calcd for C22H17NO: C, 84.8; H, 5.51; N,4.50. Found: C, 84.4; H. 5.73; N, 4.30.

後処理

  1. extractionThe mixture was then extracted into diethyl ether (500 mL)
  2. washwashed with H2O (3×300 mL)
  3. dry with materialdried (Na2SO4)
  4. customthe solvent removed under vacuum
  5. customThe resulting yellow oil was dried under high vacuum (4 h)
  6. dissolutionredissolved in hot diethyl ether (70 mL)
  7. waitThe solution was kept at -20° C. for 24 h
  8. filtrationfiltered
  9. washthe solid washed with ice-cold hexand (2×50 mL)

出典と根拠

ORDレコード
ord-ce9726b62b0645b095f9d088eb09e359
出典データセット
uspto-grants-2000_01
特許番号
US06013434

反応ノート

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