Triethylamine → Phenethylisoselenocyanate

HRID 2273814Notes

Reaction equation

HRID 2273814 reaction equation
[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

Participants

7

Reactant 5

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

Product 1

HCID 25060470PhenethylisoselenocyanateYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(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.

Workup

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

Sources & evidence

ORD record
ord-f48722a3444e4e91883a56bce2785fa5
Source dataset
uspto-grants-2015_09
Patent number
US09126910B2

Reaction notes

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