Triethylamine → Phenylbutyl Isoselenocyanate

HRID 508385Notes

Reaction equation

HRID 508385 reaction equation
[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

Participants

7

Reactant 5

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

Product 1

HCID 25015746Phenylbutyl 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 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.

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-8f04ac3545244525bc1f6b7a7356bde6
Source dataset
uspto-grants-2015_08
Patent number
US09096505B2

Reaction notes

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