m-Chloroperbenzoic acid → HCID 131717972, compound

HRID 1587553Notes

Reaction equation

HRID 1587553 reaction equation
C[S:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][CH2:10][CH2:11][CH2:12][NH:13][CH2:14][CH2:15][CH2:16][NH:17][C:18]2[CH:23]=[CH:22][C:21]([S:24]C)=[CH:20][CH:19]=2)=[CH:5][CH:4]=1.[Cl:26]C1C=CC=C(C(OO)=O)C=1.[OH-].[Ca+2].[OH-]>C(Cl)(Cl)Cl>[ClH:26].[ClH:26].[ClH:26].[SH:2][C:3]1[CH:4]=[CH:5][C:6]([NH:9][CH2:10][CH2:11][CH2:12][NH:13][CH2:14][CH2:15][CH2:16][NH:17][C:18]2[CH:19]=[CH:20][C:21]([SH:24])=[CH:22][CH:23]=2)=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 6093208Calcium HydroxideHCID 53945989HCID 53945989, compound

Product 1

HCID 131717972HCID 131717972, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Dissolve 1,9-bis[4-methylmercaptophenyl]-1,5,9-triazanonane (1.88 g, 5 mmol) in chloroform (20 mL) and treat with metachloroperbenzoic acid (863 mg, 5 mmol). Add calcium hydroxide (556 mg, 7.5 mmol) and stir for 15 minutes. Filter and evaporate the solvent in vacuo. Dissolve the residue in trifluoroacetic anhydride (10 mL) and heat at reflux for 30 minutes. Evaporate the volatiles in vacuo and dissolve the residue in a mixture of methanol-triethylamine (1:1, 100 mL) and evaporate the solvent in vacuo. Dissolve the resdiue in chloroform, wash with saturated ammonium chloride and dry (MgSO4). Evaporate the solvent in vacuo to give the crude 1,9-bis[(4-mercaptophenyl)]-1,5,9 triazanonane.

Workup

  1. filtrationFilter
  2. customevaporate the solvent in vacuo
  3. dissolutionDissolve the residue in trifluoroacetic anhydride (10 mL)
  4. temperatureheat
  5. temperatureat reflux for 30 minutes
  6. customEvaporate the volatiles in vacuo
  7. dissolutiondissolve the residue
  8. additionin a mixture of methanol-triethylamine (1:1, 100 mL)
  9. customevaporate the solvent in vacuo
  10. dissolutionDissolve the resdiue in chloroform
  11. washwash with saturated ammonium chloride
  12. dry with materialdry (MgSO4)
  13. customEvaporate the solvent in vacuo

Sources & evidence

ORD record
ord-24e2cf8b6462438fbf12065f320ed6aa
Source dataset
uspto-grants-1993_06
Patent number
US05217964

Reaction notes

Loading…