Potassium ethylxanthate → HCID 178421593, compound

HRID 1903139Notes

Reaction equation

HRID 1903139 reaction equation
[CH3:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[C:4]([NH2:12])[C:3]=1[NH2:13].C(O[C:17]([S-])=[S:18])C.[K+]>O>[CH3:1][C:2]1[C:3]2[N:13]=[C:17]([SH:18])[NH:12][C:4]=2[CH:5]=[C:6]2[C:11]=1[CH:10]=[CH:9][CH:8]=[CH:7]2

Participants

4

Reactant 2

HCID 2735045Potassium ethylxanthateHCID 13343754HCID 13343754, compound

Product 1

HCID 178421593HCID 178421593, compoundYield 48.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

16.9 g of 1-methyl-2,3-diamino-naphthalene (crude base) were suspended in 250 ml of alcohol in a 500 ml sulfonation flask equipped with stirrer, thermometer and reflux condenser and, after adding 25 ml of water as well as 18.8 g of potassium ethylxanthate, recrystallized from isopropanol, boiled at reflux overnight. The insoluble particles were removed by filtration, the solution was diluted with 200 ml of water and made neutral with 10-15 ml of glacial acetic acid. After stirring at 60°-70° C. for 1 hour, the mixture was cooled and suction filtered. There were obtained 10.2 g (48.5% of theory) of 4-methyl-1H-naphth(2,3-d)imidazole-2-thiol with a melting point above 300° C.

Workup

  1. customequipped with stirrer
  2. temperaturethermometer and reflux condenser
  3. customrecrystallized from isopropanol
  4. temperatureat reflux overnight
  5. customThe insoluble particles were removed by filtration
  6. additionthe solution was diluted with 200 ml of water
  7. temperaturethe mixture was cooled
  8. filtrationsuction filtered

Sources & evidence

ORD record
ord-f285d88dc3564523b8c81962bb502666
Source dataset
uspto-grants-1984_03
Patent number
US04435406

Reaction notes

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