Hydroxylamine → HCID 14208182、化合物

HRID 477436ノート

反応式

HRID 477436 の反応式
[CH3:1][N:2]([CH:4](O)[CH3:5])[CH3:3].C1(C)C=CC(S(O)(=O)=[O:14])=CC=1.NO.S(C1C=CC(C)=CC=1)([O-])(=O)=O.[NH4+].[CH2:32]([CH:45]1[CH2:49][CH:48]=[CH:47][O:46]1)[CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH3:44].C(=O)([O-])[O-].[Na+].[Na+]>C(Cl)(Cl)(Cl)Cl.C(Cl)(Cl)Cl.CO>[CH2:32]([CH:45]1[CH2:49][CH2:48][CH:47]([O:14][CH2:5][CH2:4][N:2]([CH3:3])[CH3:1])[O:46]1)[CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH3:44]

参加物

9

反応物 6

HCID 787HydroxylamineHCID 6101p-Toluenesulfonic acidHCID 10340Sodium CarbonateHCID 10313070Dimethylamino-ethanolHCID 14208181HCID 14208181、化合物HCID 15911366Benzenesulfonic acid, 4-methyl-, ammonium salt (1:1)

生成物 1

HCID 14208182HCID 14208182、化合物

試薬・触媒・溶媒 2

HCID 5943Carbon Tetrachloride溶媒HCID 21584188Chloroform methanol溶媒

実験手順

A solution of 0.2 g (2.2 mmol) of dimethylamino-ethanol and 0.4 g (2.3 mmol) of dry p-toluenesulphonic acid in 50 ml of dry carbon tetrachloride was stirred at room temperature until all the amino-alcohol had been converted into its ammonium tosylate salt as determined by thin layer chromatography (chloroform:methanol 80:20 by volume). Then 0.5 g (2.mmol) of 2-tridecyl-2,3-dihydrofuran was added and the mixture was stirred in the same conditions until complete reaction of the dihydro compound as determined by TLC (petroleum ether:ether 90:10 by volume). After evacuation of the solvent under reduced pressure, the residue was diluted by 20 ml of a saturated aqueous sodium carbonate solution and extracted several times with diethyl ether. The diethyl ether phase was washed with water until neutrality, dried on anhydrous magnesium sulphate and filtered. The residue, after evaporation of water, was chromatographed on silica gel using successively mixtures of methanol:chloroform, from 1:99 to 20:80 by volume, to yield 0.5 g of the cis-trans title compound as an oil. NMR (80 MHz, CDCl3, HMDS*) δ 0.82 (t, 3H, CH3 alkyl chain) 1.17 (large s, 22H, (CH2)11) 1.92 (m, 4 H, CH2 --C--O) 2.17 (s, 6H, CH3N) 2.42 (m, 4H, CH2N+ ##STR10## 3.25-3.87 (m, 2H, CH2O) 3.92 (m, 1H, CH--O) 4.95 (m, 1H, ##STR11##

後処理

  1. extractionextracted several times with diethyl ether
  2. washThe diethyl ether phase was washed with water until neutrality
  3. dry with materialdried on anhydrous magnesium sulphate
  4. filtrationfiltered
  5. customThe residue, after evaporation of water
  6. customwas chromatographed on silica gel using successively mixtures of methanol

出典と根拠

ORDレコード
ord-a9b7590c5b8042f984ed4a30cc565128
出典データセット
uspto-grants-1989_12
特許番号
US04888337

反応ノート

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