Triethylamine → Phenylbutyl Isoselenocyanate

HRID 2273815노트

반응식

HRID 2273815 반응식
[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][NH:11][CH:12]=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:43])C1C=CC=CC=1>C(Cl)Cl>[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][N:11]=[C:12]=[Se:43])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

참가 물질

7

반응물 5

HCID 8471TriethylamineHCID 94429TriphosgeneHCID 6326970SeleniumHCID 12506035Benzyl IsoselenocyanateHCID 20716133Phenylbutyl formamide

생성물 1

HCID 25015746Phenylbutyl Isoselenocyanate수율 95%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

A mixture of phenylbutyl formamide (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 2c as an oil. 1H NMR (CDCl3) δ 1.74-1.76 (m, 4H), 2.66 (t, 2H, J=6.6 Hz), 3.60 (t, 2H, J=5.6 Hz), 7.15-7.32 (m, 5H); HRMS (EI) calcd for C11H13NSe, 239.0208; found, 239.0211.

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-f1c3a843cc4f48998512b3d96c5cc4e5
출처 데이터셋
uspto-grants-2015_09
특허 번호
US09126910B2

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