Triethylamine → HCID 18334081、化合物

HRID 2269497ノート

反応式

HRID 2269497 の反応式
[N+:1]([C:4]1[CH:5]=[C:6]([C:10]([C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=2)=O)[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].[C:20]([NH2:29])([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)([CH3:22])[CH3:21].C(N(CC)CC)C.C([BH3-])#N.[Na+]>ClCCl.C(OCC)(=O)C.[Ti](Cl)(Cl)(Cl)Cl.C(O)(=O)C.C(O)C>[CH3:19][O:18][C:15]1[CH:16]=[CH:17][C:12]([CH:10]([C:6]2[CH:7]=[CH:8][CH:9]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=2)[NH:29][C:20]([CH3:22])([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH3:21])=[CH:13][CH:14]=1

参加物

10

反応物 4

HCID 8471TriethylamineHCID 68509CumylamineHCID 794540(4-Methoxyphenyl)(3-nitrophenyl)methanoneHCID 5003444Sodium cyanoborohydride

生成物 1

HCID 18334081HCID 18334081、化合物収率 38%

試薬・触媒・溶媒 5

HCID 24193Titanium Tetrachloride触媒HCID 176Acetic Acid溶媒HCID 702Ethanol溶媒HCID 6344Dichloromethane溶媒2 回HCID 8857Ethyl Acetate溶媒

実験手順

2.57 g of 4-methoxyphenyl 3-nitrophenyl ketone, 1.35 g of cumyl amine and 1.35 g of triethylamine were dissolved in 50 ml of dichloromethane, and then 30 ml of a solution of 1.65 ml of titanium tetrachloride in dichloromethane was added dropwise whilst ice cooling. The reaction mixture was stirred at room temperature for 2 hours and was then heated under reflux for 3 hours. The reaction mixture was allowed to cool, after which it was diluted with 150 ml of ethyl acetate. The insoluble matter was then filtered off. The filtrate was washed with a saturated solution of sodium hydrogencarbonate and with a saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate and distilled under reduced pressure to remove the solvent. Following a similar reaction, separation and purification procedure to that described in Example (1a), the resulting brown oil, 100 ml of ethanol 2.51 g of sodium cyanoborohydride and 2.58 ml of acetic acid were reacted, to obtain 1.43 g of the title compound as a yellow oil.

後処理

  1. temperaturewas then heated
  2. temperatureunder reflux for 3 hours
  3. temperatureto cool
  4. filtrationThe insoluble matter was then filtered off
  5. washThe filtrate was washed with a saturated solution of sodium hydrogencarbonate and with a saturated aqueous solution of sodium chloride
  6. dry with materialdried over anhydrous magnesium sulfate
  7. distillationdistilled under reduced pressure
  8. customto remove the solvent
  9. customa similar reaction, separation and purification procedure to

出典と根拠

ORDレコード
ord-fbc68857273849b89ee276d2977c81e1
出典データセット
uspto-grants-2001_12
特許番号
US06329405B1

反応ノート

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