Sulfur → HCID 13764030, compound

HRID 1681411Notes

Reaction equation

HRID 1681411 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][C:14]([N:17]4[CH:21]=[CH:20][N:19]=[C:18]4[CH3:22])=[CH:13][CH:12]=3)[C:5]2=[CH:4][N:3]=1.[S]>ClC1C=CC=CC=1Cl>[CH3:1][C:2]1[N:6]2[CH:7]=[CH:8][CH:9]=[C:10]([C:11]3[CH:12]=[CH:13][C:14]([N:17]4[CH:21]=[CH:20][N:19]=[C:18]4[CH3:22])=[CH:15][CH:16]=3)[C:5]2=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 5362487SulfurHCID 13764020HCID 13764020, compound

Product 1

HCID 13764030HCID 13764030, compound

Reagents, catalysts & solvents 1

HCID 72391,2-DichlorobenzeneSolvent

Procedure

Combine 24 g (82.7 mmol) of the product of Example III with 10 g (0.31 mol) of sulfur in 500 ml of 1,2-dichlorobenzene and heat to reflux under nitrogen for 13 hr. Cool to room temperature and extract with 2×500 ml of 10% hydrochloric acid. Combine the extracts and wash with 1 liter of methylene chloride and 500 ml of ethyl acetate. The aqueous phase is treated with charcoal, filtered, neutralized with sodium hydroxide, and extracted with 2×500 ml of methylene chloride. Dry the combined extracts over magnesium sulfate and charcoal treat. Concentrate under vacuum to 200 ml total volume and isolate the title compound by column chromatography on 300 g of silica gel using 2% methanol/methylene chloride as solvent.

Workup

  1. temperatureto reflux under nitrogen for 13 hr
  2. extractionextract with 2×500 ml of 10% hydrochloric acid
  3. washwash with 1 liter of methylene chloride and 500 ml of ethyl acetate
  4. additionThe aqueous phase is treated with charcoal
  5. filtrationfiltered
  6. extractionextracted with 2×500 ml of methylene chloride
  7. dry with materialDry the combined extracts over magnesium sulfate and charcoal
  8. additiontreat
  9. concentrationConcentrate under vacuum to 200 ml total volume

Sources & evidence

ORD record
ord-1366d769d6ba4171bc01973cf0d0cd65
Source dataset
uspto-grants-1992_12
Patent number
US05171858

Reaction notes

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