Hydroxylamine → HCID 14208182, 화합물

HRID 477436노트

반응식

HRID 477436 반응식
[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]

참가 물질

9

반응물 6

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

생성물 1

HCID 14208182HCID 14208182, 화합물

시약·촉매·용매 2

HCID 5943Carbon Tetrachloride용매HCID 21584188Chloroform methanol용매

실험 절차

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##

후처리

  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

출처 및 근거

ORD 기록
ord-a9b7590c5b8042f984ed4a30cc565128
출처 데이터셋
uspto-grants-1989_12
특허 번호
US04888337

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