Iodine → 3-Mercapto-N,N-dimethylbenzamide

HRID 230852Notes

Reaction equation

HRID 230852 reaction equation
II.[CH3:3][N:4]([CH3:17])[C:5]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1S(Cl)(=O)=O)=[O:6].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[S:37]([O-])([O-])=O.[Na+].[Na+]>O1CCOCC1>[SH:37][C:9]1[CH:8]=[C:7]([CH:12]=[CH:11][CH:10]=1)[C:5]([N:4]([CH3:17])[CH3:3])=[O:6]

Participants

6

Reactant 4

HCID 807IodineHCID 11776TriphenylphosphineHCID 24437Sodium SulfiteHCID 131402112-(Dimethylcarbamoyl)benzene-1-sulfonyl chloride

Product 1

HCID 577632243-Mercapto-N,N-dimethylbenzamide

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Iodine (1 g) was added to a stirred solution of 3-[(dimethylamino)carbonylbenzenesulfonyl chloride (2 g) (Borthwick et al, J. Med. Chem 2002, 45(1), 1-18) and triphenylphosphine (8.4 g) in 1,4-dioxane at 0° C. The mixture was stirred for 0.5 h at ambient temperature. The mixture was poured into a sodium sulphite solution (50 ml), extracted into ethyl acetate (2×30 ml) and washed with 2N sodium hydroxide solution (2×40 ml). The alkaline extracts were acidified and re-extracted into dichloromethane (3×50 ml). The extracts were washed with water (100 ml), dried (Na2SO4) and evaporated to give the title compound as a colourless solid (1.1 g).

Workup

  1. extractionextracted into ethyl acetate (2×30 ml)
  2. washwashed with 2N sodium hydroxide solution (2×40 ml)
  3. extractionre-extracted into dichloromethane (3×50 ml)
  4. washThe extracts were washed with water (100 ml)
  5. dry with materialdried (Na2SO4)
  6. customevaporated

Sources & evidence

ORD record
ord-14e572f5d30844efa61ff553d50f8b4c
Source dataset
uspto-grants-2009_07
Patent number
US07566786B2

Reaction notes

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