Sulfur → HCID 13764028, compound

HRID 1494377Notes

Reaction equation

HRID 1494377 reaction equation
[CH3:1][C:2]1[N:6]2[CH2:7][CH2:8][CH:9]=[C:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[C:5]2=[CH:4][N:3]=1.[S]>C1C2C(CCCC2)CCC1>[CH3:1][C:2]1[N:6]2[CH:7]=[CH:8][CH:9]=[C:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[C:5]2=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 5362487SulfurHCID 13764013HCID 13764013, compound

Product 1

HCID 13764028HCID 13764028, compound

Reagents, catalysts & solvents 1

HCID 7044DecalinSolvent

Conditions

Temperature
185 °C

Procedure

Add 250 g (1.2 mol) of the product from Example XVIII to a solution of 75 g (2.3 mol) of sulfur in 1.5 liters of decalin and heat to 180-190° C. under nitrogen for 6 hr. Cool to room temperature and extract with 2-1.5 liters of 2N sulfuric acid. Combine the acid extracts and make basic with potassium hydroxide, then wash with 2×1 liter of methylene chloride. Combine the methylene chloride extracts, dry over sodium sulfate, treat with charcoal, and remove the solvent in vacuo. Crystallize the residue from ether to provide the title compound.

Workup

  1. temperatureCool to room temperature
  2. extractionextract with 2-1.5 liters of 2N sulfuric acid
  3. washwash with 2×1 liter of methylene chloride
  4. dry with materialdry over sodium sulfate
  5. additiontreat with charcoal
  6. customremove the solvent in vacuo
  7. customCrystallize the residue from ether

Sources & evidence

ORD record
ord-1b5a29d7a2d84ed38b9847e08284f375
Source dataset
uspto-grants-1991_06
Patent number
US05026712

Reaction notes

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