Iodine → Di-(2,4-dinitrobenzyl) disulfide

HRID 726421Notes

Reaction equation

HRID 726421 reaction equation
II.[N+:3]([C:6]1[CH:13]=[C:12]([N+:14]([O-:16])=[O:15])[CH:11]=[CH:10][C:7]=1[CH2:8][SH:9])([O-:5])=[O:4]>ClCCl>[N+:3]([C:6]1[CH:13]=[C:12]([N+:14]([O-:16])=[O:15])[CH:11]=[CH:10][C:7]=1[CH2:8][S:9][S:9][CH2:8][C:7]1[CH:10]=[CH:11][C:12]([N+:14]([O-:16])=[O:15])=[CH:13][C:6]=1[N+:3]([O-:5])=[O:4])([O-:5])=[O:4]

Participants

4

Reactant 2

HCID 807IodineHCID 107038212,4-Dinitrobenzyl mercaptan

Product 1

HCID 10550343Di-(2,4-dinitrobenzyl) disulfideYield 82%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of iodine (0.321 g, 1.26 mmol) and 2,4-dinitrobenzyl mercaptan (0.493 g, 2.3 mmol) in dichloromethane (25 cm3) was stirred at room temperature ovemight. More dichloromethane (25 cm3) was added and the products were washed with 0.2 mol dm-3 sodium hydrogen sulfite (20 cm3), water (20 cm3) and saturated aqueous sodium hydrogen carbonate (20 cm3). The dried (MgSO4) organic layer was concentrated under reduced pressure and the residue was crystallized from absolute ethanol to give di-(2,4-dinitrobenzyl) disulfide 19 (0.402 g, 82%) (Found: C, 39.4; H, 2.4; N, 13.0. C14H10N4O8 S2 requires: C, 39.4; H, 2.4; N, 13.1%), m.p. 108°-109° C.; δH [CDCl3 ] 4.22 (4 H, s), 7.66 (2 H, d, J 8.5), 8.46 (2 H, dd, J 2.4 and 8.4), 8.91 (2H, d, J2.4);δC [CDCl3 ] 40.0, 121.1, 127.5, 133.9, 139.4, 147.4, 148.0.

Workup

  1. washthe products were washed with 0.2 mol dm-3 sodium hydrogen sulfite (20 cm3), water (20 cm3) and saturated aqueous sodium hydrogen carbonate (20 cm3)
  2. dry with materialThe dried (MgSO4) organic layer
  3. concentrationwas concentrated under reduced pressure
  4. customthe residue was crystallized from absolute ethanol

Sources & evidence

ORD record
ord-f5ee5a1ac3a244a0a55d4620949039e8
Source dataset
uspto-grants-1998_01
Patent number
US05708161

Reaction notes

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