HCID 13377158, compound → HCID 13377159, compound

HRID 1194682Notes

Reaction equation

HRID 1194682 reaction equation
[NH4+]=S.[CH3:3][C:4]1[C:8]2[CH:9]=[C:10]([N+:16]([O-:18])=[O:17])[CH:11]=[C:12]([N+:13]([O-])=O)[C:7]=2[S:6][CH:5]=1>C(O)C.O>[CH3:3][C:4]1[C:8]2[CH:9]=[C:10]([N+:16]([O-:18])=[O:17])[CH:11]=[C:12]([NH2:13])[C:7]=2[S:6][CH:5]=1

Participants

4

Reactant 1

HCID 13377158HCID 13377158, compound

Product 1

HCID 13377159HCID 13377159, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

453 ml of a 20% strength ammonium sulphide solution (1.33 moles of (NH4)2S) are added dropwise to a suspension of 0.4 mole of 3-methyl-5,7-dinitrobenzothiophene in 1,400 ml of ethanol at 55°-60° C. in the course of 45 minutes, and the mixture is then heated at the boiling point for 15 minutes. The mixture is then diluted with 1,400 ml of water and cooled to 0° C. and the crystalline product is filtered off with suction. For purification, the crystals are dissolved in methylene chloride and the solution is filtered over a silica gel column (eluting agent: methylene chloride/cyclohexane 9:11). The substance obtained from the combined eluates is recrystallised from isopropanol.

Workup

  1. temperaturethe mixture is then heated at the boiling point for 15 minutes
  2. filtrationthe crystalline product is filtered off with suction
  3. customFor purification
  4. dissolutionthe crystals are dissolved in methylene chloride
  5. filtrationthe solution is filtered over a silica gel column (eluting agent: methylene chloride/cyclohexane 9:11)
  6. customThe substance obtained from the combined eluates
  7. customis recrystallised from isopropanol

Sources & evidence

ORD record
ord-896f579e7fe34856961953cfb618439f
Source dataset
uspto-grants-1989_03
Patent number
US04816461

Reaction notes

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