Pyridine → HCID 1377347, compound

HRID 1726874Notes

Reaction equation

HRID 1726874 reaction equation
[I:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=1.N1C=CC=CC=1.[C:15]1([S:21](Cl)(=[O:23])=[O:22])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>C(#N)C>[I:1][C:2]1[CH:8]=[CH:7][C:5]([NH:6][S:21]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)(=[O:23])=[O:22])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 7369Benzenesulfonyl chlorideHCID 108934-Iodoaniline

Product 1

HCID 1377347HCID 1377347, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

To a solution of 2.0 g of 4-iodoaniline (9.13 mmol) in 40 ml of acetonitrile there are added 1.48 ml of pyridine (18.26 mmol) and then, dropwise, a solution of 1.28 ml of benzenesulphonyl chloride (10 mmol) in 20 ml of acetonitrile. The reaction mixture is stirred overnight at ambient temperature and the acetonitrile is evaporated off under reduced pressure. The residue is taken up in 1N HCl and extracted with ethyl acetate. The organic phase is washed with brine, dried (MgSO4) and evaporated under reduced pressure. The oily residue obtained is triturated in isopropyl ether until the title product crystallises.

Workup

  1. customthe acetonitrile is evaporated off under reduced pressure
  2. extractionextracted with ethyl acetate
  3. washThe organic phase is washed with brine
  4. dry with materialdried (MgSO4)
  5. customevaporated under reduced pressure
  6. customThe oily residue obtained
  7. customis triturated in isopropyl ether until the title product
  8. customcrystallises

Sources & evidence

ORD record
ord-a31064b6d8ec4d28a3f4e06be116ba1b
Source dataset
uspto-grants-2009_02
Patent number
US07494995B2

Reaction notes

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