Triethylamine → Phenylhexyl Isoselenocyanate

HRID 508386Notes

Reaction equation

HRID 508386 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, 21-1, 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-677e072b83354530ab2908f7b7189f6f
Source dataset
uspto-grants-2015_08
Patent number
US09096505B2

Reaction notes

Loading…