m-Chloroperbenzoic acid → HCID 22394144, compound

HRID 1071555Notes

Reaction equation

HRID 1071555 reaction equation
[OH2:1].[NH:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[N:4]=[C:3]1[S:11][CH2:12][C:13]1[C:14]([NH2:19])=[N:15][CH:16]=[CH:17][CH:18]=1.N1C2C=CC=CC=2N=C1SCC1C(N)=NC=CC=1.ClC1C=CC=C(C(OO)=[O:46])C=1>ClCCl>[NH:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[N:4]=[C:3]1[S:11]([CH2:12][C:13]1[C:14]([NH2:19])=[N:15][CH:16]=[CH:17][CH:18]=1)(=[O:46])=[O:1]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acid2×HCID 69793526HCID 69793526, compound

Product 1

HCID 22394144HCID 22394144, compoundYield 5.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A suspension of 4.0 g (15 mmole) of 3-[(1H-benzimidazol-2-ylthio)methyl]-2-pyridinamine hemihydrate (see Example 79) in 50 ml of dichloromethane was cooled in an ice bath. A solution of 3.0 g (15 mmole) of ca. 85% m-chloroperbenzoic acid in the minimum amount of dichloromethane needed to form a solution was then added dropwise with stirring. After addition was complete, another 3.0 g of ca. 85% m-chloroperbenzoic acid was added. The reaction was quenched with 10 drops of dimethylsulfide. The mixture was washed with saturated aqueous sodium bicarbonate. The organic phase was concentrated in vacuo and chromatographed on silica gel (using ethanol-dichloromethane-triethylamine as eluent). Initial fractions yielded 249 mg of the title sulfone. Structure assignment was supported by the nmr and infrared spectra and by elemental analysis. Analysis. Calc'd. for C12H12N4SO2: C, 54.15; H, 4.19; N, 19.43. Found: C, 53.79; H, 4.09; N, 19.29.

Workup

  1. temperaturewas cooled in an ice bath
  2. customto form a solution
  3. additionwas then added dropwise
  4. additionAfter addition
  5. customThe reaction was quenched with 10 drops of dimethylsulfide
  6. washThe mixture was washed with saturated aqueous sodium bicarbonate
  7. concentrationThe organic phase was concentrated in vacuo
  8. customchromatographed on silica gel (using ethanol-dichloromethane-triethylamine as eluent)

Sources & evidence

ORD record
ord-9570a6b7ead54be4bc77a4f972eb2d21
Source dataset
uspto-grants-2005_06
Patent number
US06906078B2

Reaction notes

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