Methyl iodide → HCID 53779776, compound

HRID 361555Notes

Reaction equation

HRID 361555 reaction equation
Cl[C:2]1[C:7]([Cl:8])=[CH:6][C:5]([N+:9]([O-:11])=[O:10])=[CH:4][N:3]=1.N[C:13](N)=[S:14].[OH-].[Na+].CI>C(O)C>[Cl:8][C:7]1[C:2]([S:14][CH3:13])=[N:3][CH:4]=[C:5]([N+:9]([O-:11])=[O:10])[CH:6]=1

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 14798Sodium HydroxideHCID 2723790ThioureaHCID 27631062,3-Dichloro-5-nitropyridine

Product 1

HCID 53779776HCID 53779776, compoundYield 70.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
10 °C

Procedure

2,3-Dichloro-5-nitropyridine (7.90 g, 0.041 mol) (Synthesis, 1990, 499) was dissolved in ethanol (150 ml) and was treated with thiourea (3.43 g, 0.045 mol). The resultant mixture was then heated to reflux with stirring under argon. After 3 h, the reaction mixture was allowed to cool, and was left stirring at room temp. for 16 h. 10% Sodium hydroxide solution (160 ml) was then added and the reaction mixture was heated to reflux with stirring. After 1 h, the reaction mixture was cooled to 10° C., and methyl iodide (2.80 ml, 0.045 mol) was added. After 1 h, the resultant precipitate was filtered off to give the title compound as an orange solid (5.90 g, 70%).

Workup

  1. temperatureto reflux
  2. temperatureto cool
  3. waitwas left
  4. stirringstirring at room temp. for 16 h
  5. temperaturethe reaction mixture was heated
  6. temperatureto reflux
  7. stirringwith stirring
  8. waitAfter 1 h
  9. waitAfter 1 h
  10. filtrationthe resultant precipitate was filtered off

Sources & evidence

ORD record
ord-9e5e3d2cc2c64568ad8b6cb2e0f4d722
Source dataset
uspto-grants-1999_02
Patent number
US05866586

Reaction notes

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