HCID 14033016, compound → HCID 14033017, compound

HRID 1194726Notes

Reaction equation

HRID 1194726 reaction equation
[Cl:1][C:2]([C:6]1[CH:7]=[C:8]([CH3:15])[CH:9]=[C:10]([N+:12]([O-])=O)[CH:11]=1)=[C:3]([Cl:5])[Cl:4].[NH4+]=S>C(O)C.O>[CH3:15][C:8]1[CH:9]=[C:10]([CH:11]=[C:6]([C:2]([Cl:1])=[C:3]([Cl:4])[Cl:5])[CH:7]=1)[NH2:12]

Participants

4

Reactant 1

HCID 14033016HCID 14033016, compound

Product 1

HCID 14033017HCID 14033017, compoundYield 96.3%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

To a warm solution of 3-(trichlorovinyl)-5-nitrotoluene (10.95 g) in 150 ml of ethanol, an aqueous solution of ammonium sulfide (30 ml of a commercial 46-52% aqueous solution diluted to 90 ml with water) was added in one portion. The resulting heterogeneous solution was heated in a 100° C. oil bath for 30 minutes. The hot reaction mixture was filtered and the precipitate thoroughly washed with ethanol. The filtrate was diluted with 1.2 L of brine and then extracted with methylene chloride (2×400 ml). The combined organic layers were washed with brine and dried over anhydrous magnesium sulfate. Concentration afforded 9.36 g of an oil.

Workup

  1. additionwas added in one portion
  2. filtrationThe hot reaction mixture was filtered
  3. washthe precipitate thoroughly washed with ethanol
  4. additionThe filtrate was diluted with 1.2 L of brine
  5. extractionextracted with methylene chloride (2×400 ml)
  6. washThe combined organic layers were washed with brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationConcentration

Sources & evidence

ORD record
ord-c5a4d969b3154c799e90339c10822419
Source dataset
uspto-grants-1989_03
Patent number
US04816469

Reaction notes

Loading…