Hydrochloric Acid → 773U82 Hydrochloride

HRID 1381805ノート

反応式

HRID 1381805 の反応式
[CH:1]1[C:15]2=[C:16]3[C:8]([C:9]4[C:14]2=[CH:13][CH:12]=[CH:11][CH:10]=4)=[CH:7][CH:6]=[CH:5][C:4]3=C(C=O)C=1.[C:19]1([CH3:29])C=CC(S(O)(=O)=O)=CC=1.[BH3-][C:31]#[N:32].[Na+].CC1C(Br)=C(O)C(Br)=CC=1[C:44]1([C:55]2[CH:56]=C(Br)C(O)=C(Br)[C:60]=2C)[O:54]S(=O)(=O)C2C=CC=CC1=2.[ClH:65].CC[OH:68]>O.C1(C)C=CC=CC=1>[ClH:65].[CH:7]1[C:8]2=[C:16]3[C:15]([C:14]4[C:9]2=[CH:10][CH:11]=[CH:12][CH:13]=4)=[CH:1][CH:29]=[CH:19][C:4]3=[C:5]([CH2:31][NH:32][C:55]([CH3:60])([CH2:44][OH:54])[CH2:56][OH:68])[CH:6]=1

参加物

9

反応物 6

HCID 313Hydrochloric Acid3 回HCID 702Ethanol3 回HCID 6101p-Toluenesulfonic acidHCID 6451Bromocresol GreenHCID 1811133-FluoranthenecarboxaldehydeHCID 5003444Sodium cyanoborohydride2 回

生成物 1

HCID 3024572773U82 Hydrochloride収率 66%

試薬・触媒・溶媒 2

HCID 962Water溶媒3 回HCID 1140Toluene溶媒

実験手順

To a 2 L Erlenmeyer flask was added 3-fluoranthenecarbaldeyde (11.51 g, 50 mmol) 2-methyl-2-amino-1,3-propanediol (Aldrich, 5.52 g, 52.5 mmol), p-toluenesulfonic acid.H2O (Eastman Kodak Co., Rochester, NY, 14650, 0.1 g, 0.5 mmol), and PhCH3 (500 mL). The mixture was warmed to reflux for a few minutes and H2O (2-3 mL) was driven off. The resulting golden colored solution was allowed to cool to RT, diluted with abs. EtOH (500 mL) and stirred overnight. NaBH3CN (Aldrich, 95%, 1.57 g, 25 mmol) was added to the reaction. After the NaBH3CN dissolved, an indicator (bromocresol green, Eastman, 5 mg) was added. To the resulting added. To the resulting blue solution was added 5 drops of 1M solution of HCl gas in absolute EtOH every 15 minutes. After 3 days the indicator turned green then yellow and voluminous white precipitate was present in the flask. To the flask was then added 1M HCl gas (10 mL) in abs. EtOH, and H2O (10 mL). The liquid was then removed by rotary evaporation to give a yellow solid. The solid was shaken with 20% HCl solution (500 mL) and collected by filtration. The resulting solid was washed with additional 20% HCl solution (250 mL) and then with CH2Cl2 (4×250 mL), pressed and then sucked dry. The slightly yellow solid was then recrystallized from CH3OH/Et2O to give 11.80 g (66%) of 2-((3-fluoranthenylmethyl)amino)-2-methyl-1,3-propanediol hydrochloride mp 262°-265° (dec), (C, H, Cl, N).

後処理

  1. temperatureThe mixture was warmed
  2. temperatureto reflux for a few minutes
  3. additiondiluted with abs
  4. additionTo the resulting added
  5. customThe liquid was then removed by rotary evaporation
  6. customto give a yellow solid
  7. filtrationcollected by filtration
  8. washThe resulting solid was washed with additional 20% HCl solution (250 mL)
  9. customsucked dry
  10. customThe slightly yellow solid was then recrystallized from CH3OH/Et2O

出典と根拠

ORDレコード
ord-c904f3c9eac04891a52f567667f6e4ca
出典データセット
uspto-grants-1989_02
特許番号
US04803222

反応ノート

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