Iodine → Hydroxy(4-(((4-(hydroxy(oxido)amino)benzyl)dithio)methyl)phenyl)azane oxide

HRID 1376852Notes

Reaction equation

HRID 1376852 reaction equation
[N+:1]([C:4]1[CH:11]=[CH:10][C:7]([CH2:8][SH:9])=[CH:6][CH:5]=1)([O-:3])=[O:2].II>C(Cl)Cl.C(N(CC)CC)C>[N+:1]([C:4]1[CH:11]=[CH:10][C:7]([CH2:8][S:9][S:9][CH2:8][C:7]2[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:11][CH:10]=2)=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

5

Reactant 2

HCID 807IodineHCID 1936194-Nitrobenzyl mercaptan

Product 1

HCID 334132Hydroxy(4-(((4-(hydroxy(oxido)amino)benzyl)dithio)methyl)phenyl)azane oxideYield 84.4%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Conditions

Temperature
25 °C

Procedure

1.0 g of p-nitrobenzylmercaptan was dissolved in 30 of methylene chloride and 0.83 ml of triethylamine and 750 mg of iodine were added while maintaining the temperature at 25° C. and stirring for 10 minutes. After washing with N hydrochloric acid, the organic phase was dried and the solvent was evaporated. 20 ml of ether were added to the residue, and after stirring for 10 minutes, separating and drying, 839 mg of p-nitrobenzyl disulfide melting at 126° C. were obtained.

Workup

  1. additionwere added
  2. washAfter washing with N hydrochloric acid
  3. customthe organic phase was dried
  4. customthe solvent was evaporated
  5. addition20 ml of ether were added to the residue
  6. stirringafter stirring for 10 minutes
  7. customseparating
  8. customdrying

Sources & evidence

ORD record
ord-e17c81c55ff74ae89c414eac75229852
Source dataset
uspto-grants-1997_09
Patent number
US05663164

Reaction notes

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