Thiophenol → 2,5-Dimethylpyrrol-1-yl-ethyl phenyl sulfide

HRID 224655Notes

Reaction equation

HRID 224655 reaction equation
[C:1]1([S:7][CH2:8][CH2:9][NH2:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:11]1(S)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.Br.BrCCN.C(CC(=O)C)C(C)=O>C(O)(=O)C.C(N(CC)CC)C>[C:1]1([S:7][CH2:8][CH2:9][N:10]2[C:13]([CH3:14])=[CH:12][CH:11]=[C:16]2[CH3:15])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

7

Reactant 4

HCID 7969ThiophenolHCID 80352,5-HexanedioneHCID 37013Phenyl-2-aminoethyl sulfideHCID 27742172-Bromoethylamine hydrobromide

Product 1

HCID 126032572,5-Dimethylpyrrol-1-yl-ethyl phenyl sulfideYield 70%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 8471TriethylamineSolvent

Procedure

Phenylthioethylamine (5.00 g, 32.68 mmoles) prepared by reacting thiophenol and β-bromoethylamine hydrobromide in the presence of triethylamine and 3.74 g (32.68 mmoles) of acetonylacetone were heated under reflux for 4 hours in 80 ml of acetic acid. The acetic acid was distilled off under reduced pressure, and toluene was added to the residue. The mixture was distilled under reduced pressure. The resulting crude product was chromatographed on a column of silica gel using hexane/benzene as an eluent to afford 2,5-dimethylpyrrol-1-yl-ethyl phenyl sulfide (5.32 g, 22.88 mmoles, 70%).

Workup

  1. temperaturewere heated
  2. distillationThe acetic acid was distilled off under reduced pressure, and toluene
  3. additionwas added to the residue
  4. distillationThe mixture was distilled under reduced pressure
  5. customThe resulting crude product was chromatographed on a column of silica gel

Sources & evidence

ORD record
ord-0820f4ceadd6447084078fbda441b935
Source dataset
uspto-grants-1980_11
Patent number
US04233309

Reaction notes

Loading…