Iodine → Bis(thiobenzoyl) Disulfide

HRID 1636033

Reaction equation

HRID 1636033 reaction equation
II.[Na+].[C:4]([S-:12])(=[S:11])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1>C(OCC)C>[C:4]([S:12][S:12][C:4](=[S:11])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)(=[S:11])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

4

Reactant 2

HCID 807IodineHCID 11030352Sodium dithiobenzoate

Product 1

HCID 10902862Bis(thiobenzoyl) DisulfideYield 50%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

An aqueous solution of iodine (1.0 N, 100 mL) was added dropwise to a stirred aqueous solution of dithiobenzoic acid sodium salt (0.1 mol in 100 mL of water) at room temperature over 15 minutes. Diethyl ether (100 mL) was added, the organic layer separated and washed twice with water, dried (Na2SO4), filtered and concentrated in vacuo. Di(thiobenzoyl)disulfide (7.5 g, 50%) was obtained after recrystallization from hot ethanol, m.p. 89-91° C. [lit(Houben, Chem, Ber., 39, 3219-3233, (1906). m.p. 92.5° C.]. 1H-nmr (CDCl3) δ (ppm) 7.44 (m, 4H, meta-ArH); 7.62 (m, 2H, para-ArH) and 8.11 (m, 4H, ortho-ArH).

Workup

  1. customthe organic layer separated
  2. washwashed twice with water
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0b904497e7494475b98f17c298a9f463
Source dataset
uspto-grants-2003_01
Patent number
US06512081B1

Linked notes

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