Sodium benzenethiolate → 3-Nitro-6-phenylsulfanyl-imidazo[1,2-a]pyridine

HRID 1447611Notes

Reaction equation

HRID 1447611 reaction equation
[S-:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Na+].Br[C:10]1[CH:11]=[CH:12][C:13]2[N:14]([C:16]([N+:19]([O-:21])=[O:20])=[CH:17][N:18]=2)[CH:15]=1>CN1CCCC1=O>[N+:19]([C:16]1[N:14]2[CH:15]=[C:10]([S:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[CH:11]=[CH:12][C:13]2=[N:18][CH:17]=1)([O-:21])=[O:20]

Participants

4

Reactant 2

HCID 4110039Sodium benzenethiolateHCID 288758886-Bromo-3-nitroimidazo[1,2-a]pyridine

Product 1

HCID 541282433-Nitro-6-phenylsulfanyl-imidazo[1,2-a]pyridine

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A solution of 1.61 g. (0.012 mole) of sodium thiophenoxide and 2.42 g. (0.01 mole) of 6-bromo-3-nitroimidazo [1,2-a] pyridine in 10 ml. N-methylpyrolidinone is heated at 150° C. for 0.40 minutes under a nitrogen atmosphere. The cooled solution is poured onto 100 ml. of ice-water and the resultant suspension is extracted with ethyl acetate. The combined extracts are washed with saturated aqueous sodium chloride and dried over magnesium sulfate. Evaporation of the solvent to a small volume and dilution with N-hexane yields crystalline material. The solids are purified by chromatography on silica gel. Elution with methylene chloride yields pure 3-nitro 6-phenylthioimidazo [1,2-a] pyridine m.p. 108°-109° C.

Workup

  1. additionThe cooled solution is poured onto 100 ml
  2. extractionof ice-water and the resultant suspension is extracted with ethyl acetate
  3. washThe combined extracts are washed with saturated aqueous sodium chloride
  4. dry with materialdried over magnesium sulfate
  5. customEvaporation of the solvent to a small volume and dilution with N-hexane
  6. customyields crystalline material
  7. customThe solids are purified by chromatography on silica gel
  8. washElution with methylene chloride

Sources & evidence

ORD record
ord-ec243b65a4364656b2c44a4007c4a3a0
Source dataset
uspto-grants-1979_12
Patent number
US04177274

Reaction notes

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