Sodium Iodide → HCID 59402661, compound

HRID 538538Notes

Reaction equation

HRID 538538 reaction equation
[OH:1][C:2]1[CH:7]=[C:6]([C:8]#[N:9])[CH:5]=[CH:4][N:3]=1.C([O-])([O-])=O.[K+].[K+].[Na+].[I-].[Cl:18][C:19]1[CH:20]=[CH:21][C:22]2[S:26][C:25]([CH2:27]Cl)=[N:24][C:23]=2[CH:29]=1>CN(C=O)C.O>[Cl:18][C:19]1[CH:20]=[CH:21][C:22]2[S:26][C:25]([CH2:27][O:1][C:2]3[CH:7]=[C:6]([CH:5]=[CH:4][N:3]=3)[C:8]#[N:9])=[N:24][C:23]=2[CH:29]=1

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 107988395-chloro-2-(chloromethyl)-1,3-benzothiazoleHCID 178510223HCID 178510223, compound

Product 1

HCID 59402661HCID 59402661, compoundYield 7.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

2-Hydroxy-4-cyano-pyridine (240 mg, 2 mmol, 1 equiv.) was dissolved in DMF (6 ml), K2CO3 (415 mg, 3 mmol, 1.5 equiv.) and NaI (60 mg, 0.4 mmol, 0.2 equiv.) were added and the mixture was stirred at r.t. for 10 min. 5-Chloro-2-(chloromethyl)-1,3-benzothiazole (436 mg, 2 mmol, 1 equiv.) was added and the reaction mixture was stirred at 60° C. for 3 h and at r.t. overnight. By addition of H2O, brown solid precipitated, which was filtered, rinsed with H2O, dried and re-crystallised from CH3CN. Yield 280 mg (46%), mp 224-227° C., HPLC-MS (method 1): m/z 302 [M+H]+, Rt=3.80 min. By 13C-NMR analysis it was identified to be the N-alkylated derivative (Scheme 24). The DMF-H2O mother liquors were evaporated to dryness under reduced pressure and the residue was purified by column chromatography on silica, eluted with EtOAc/hexane (10%-100% gradient) to give 45 mg (7.5% yield) of a brown solid, HPLC-MS (method 1): m/z 302 [M+H]+, Rt=4.86 min. By 13C-NMR analysis, it was identified to be the desired O-alkylated derivative (Scheme 24).

Workup

  1. stirringthe reaction mixture was stirred at 60° C. for 3 h and at r.t. overnight
  2. customprecipitated
  3. filtrationwhich was filtered
  4. washrinsed with H2O
  5. customdried
  6. customre-crystallised from CH3CN
  7. customThe DMF-H2O mother liquors were evaporated to dryness under reduced pressure
  8. customthe residue was purified by column chromatography on silica
  9. washeluted with EtOAc/hexane (10%-100% gradient)

Sources & evidence

ORD record
ord-2b8af0959d354b79852cc5a4938c5043
Source dataset
uspto-grants-2014_10
Patent number
US08865736B2

Reaction notes

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