4-Chloro-1,2-dinitrobenzene → HCID 598953, compound

HRID 1074208Notes

Reaction equation

HRID 1074208 reaction equation
[SH:1][C:2]1[N:3]([CH3:7])[CH:4]=[CH:5][N:6]=1.C[O-].[Na+].[Cl:11][C:12]1[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[C:14]([N+]([O-])=O)[CH:13]=1>C(O)C>[Cl:11][C:12]1[CH:13]=[C:14]([S:1][C:2]2[N:3]([CH3:7])[CH:4]=[CH:5][N:6]=2)[C:15]([N+:18]([O-:20])=[O:19])=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 330974-Chloro-1,2-dinitrobenzeneHCID 10942334Sodium Methoxide2×HCID 178480602HCID 178480602, compound

Product 1

HCID 598953HCID 598953, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 10 g (87.7 mmoles) of 2-mercapto-1-methylimidazole in 300 ml of ethanol was added 10.4 g (193 mmoles) of sodium methoxide followed by 20.8 g (92.1 mmoles) of 1-chloro-3,4-dinitrobenzene. The mixture was stirred and refluxed for 8 hours. An additional 3 g of sodium methoxide was added and refluxing was continued for 5 more hours. The mixture was filtered hot and the filtrates concentrated in vacuo. The residue was partitioned between dichloromethane and water. The organics were dried and concentrated. The residue was recrystallized from dichloromethane and methanol to give 12.5 g (53%) of the product as yellow prisms, mp 130°-131° C.

Workup

  1. temperaturerefluxed for 8 hours
  2. temperaturerefluxing
  3. filtrationThe mixture was filtered hot
  4. concentrationthe filtrates concentrated in vacuo
  5. customThe residue was partitioned between dichloromethane and water
  6. customThe organics were dried
  7. concentrationconcentrated
  8. customThe residue was recrystallized from dichloromethane and methanol

Sources & evidence

ORD record
ord-15221b2358c64ebf9687b2a878b10fc8
Source dataset
uspto-grants-1990_11
Patent number
US04973599

Reaction notes

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