Triethylamine → Phenylhexyl Isoselenocyanate

HRID 2273816Notes

Reaction equation

HRID 2273816 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10]NC=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].[CH2:34]([N:41]=[C:42]=[Se:43])[C:35]1C=CC=CC=1>C(Cl)Cl>[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][CH2:35][CH2:34][N:41]=[C:42]=[Se:43])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

7

Reactant 5

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

Product 1

HCID 25060471Phenylhexyl IsoselenocyanateYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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 2d as an oil. 1H NMR (CDCl3) δ 1.37-1.43 (m, 2H), 1.45-1.51 (m, 2H), 1.67 (dt, 2H, J=15.2 and 7.6 Hz), 1.75 (dt, 2H, J=14.9 and 6.7 Hz), 2.64 (t, 2H, J=7.6 Hz), 3.60 (t, 2H, J=6.7 Hz), 7.19-7.25 (m, 3H), 7.32-7.40 (m, 2H); HRMS (EI) calcd for C13H17NSe, 267.0521; found, 267.0529.

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-9b60b0b60f9d4c7c977146d28dacf264
Source dataset
uspto-grants-2015_09
Patent number
US09126910B2

Reaction notes

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