Triethylamine → Phenethylisoselenocyanate

HRID 508384

반응식

HRID 508384 반응식
[C:1]1([CH2:7][CH2:8][NH:9][CH:10]=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.ClC(Cl)(OC(=O)OC(Cl)(Cl)Cl)Cl.[Se].C(N=C=[Se:41])C1C=CC=CC=1>C(Cl)Cl>[C:1]1([CH2:7][CH2:8][N:9]=[C:10]=[Se:41])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

참가 물질

7

반응물 5

HCID 8471TriethylamineHCID 94429TriphosgeneHCID 140995Formamide, N-(2-phenylethyl)-HCID 6326970SeleniumHCID 12506035Benzyl Isoselenocyanate

생성물 1

HCID 25060470Phenethylisoselenocyanate수율 95%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

(AS3.091) A mixture of phenylethylformamide (g, 1.5 mmol), triethylamine (6.4 mmol), 4 Å molecular sieves (g), triphosgene (0.8 mmol), and selenium powder (3.0 mmol) in CH2Cl2 was refluxed and worked up as mentioned for 2a. The crude residue thus obtained was purified by silica gel column chromatography (EtOAc/hexanes 2:98) to give 0.96 g (95%) of 2b as an oil. 1H NMR (CDCl3) δ 3.03 (t, 2H, J=6.9 Hz), 3.81 (t, 2H, J=6.9 Hz) 7.20-7.38 (m, 5H); HRMS (EI) calcd for C9H9NSe, 210.9895. found, 210.9892.

후처리

  1. temperaturewas refluxed
  2. customThe crude residue thus obtained
  3. customwas purified by silica gel column chromatography (EtOAc/hexanes 2:98)

출처 및 근거

ORD 기록
ord-45b41c2d14c144e5bf8cbaf74e340921
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09096505B2

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