Carbon Disulfide → HCID 178424890, compound

HRID 745568Notes

Reaction equation

HRID 745568 reaction equation
[CH3:1][C:2]1([CH3:16])[CH2:11][CH2:10][C:9]([CH3:13])([CH3:12])[C:8]2[CH:7]=[C:6]([NH2:14])[C:5]([NH2:15])=[CH:4][C:3]1=2.[OH-].[K+].[C:19](=S)=[S:20]>O>[CH3:13][C:9]1([CH3:12])[CH2:10][CH2:11][C:2]([CH3:16])([CH3:1])[C:3]2[C:8]1=[CH:7][C:6]1[N:14]=[C:19]([SH:20])[NH:15][C:5]=1[CH:4]=2

Participants

5

Reactant 3

HCID 6348Carbon DisulfideHCID 14797Potassium Hydroxide2×HCID 10262853HCID 10262853, compound

Product 1

HCID 178424890HCID 178424890, compoundYield 87.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

21.8 g of 5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2,3-naphthalenediamine were suspended in 120 ml of alcohol in a 250 ml sulfonation flask equipped with stirrer, thermometer, dropping funnel and reflux condenser. There were added dropwise thereto firstly a solution of 6.3 g of potassium hydroxide in 20 ml of water and, after stirring at room temperature for 1 hour, 8.9 g (d=1.2705) of carbon disulfide. After an additional hour, the solution was stirred and then boiled at reflux overnight. After adding 11.3 g of potassium hydroxide in 45 ml of water, the mixture was stirred for an additional 1 hour. The hot solution was then filtered through a carbon filter and the filtrate was diluted with 120 ml of water. To this was added dropwise at 60°-70° C. 60 ml of 50% acetic acid and the mixture was stirred at this temperature for an additional 1 hour. The cold suspension was suction filtered and the material on the suction filter was recrystallized from isopropanol. There were obtained 22.7 g (87.5% of theory) of 5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-1H-naphth(2,3-d)imidazole-2-thiol of melting point above 300° C.

Workup

  1. customequipped with stirrer
  2. temperaturereflux condenser
  3. additionThere were added dropwise
  4. waitAfter an additional hour
  5. temperatureat reflux overnight
  6. stirringthe mixture was stirred for an additional 1 hour
  7. filtrationThe hot solution was then filtered through a carbon
  8. filtrationfilter
  9. additionthe filtrate was diluted with 120 ml of water
  10. additionTo this was added dropwise at 60°-70° C
  11. stirring60 ml of 50% acetic acid and the mixture was stirred at this temperature for an additional 1 hour
  12. filtrationsuction filtered
  13. filtrationthe material on the suction filter
  14. customwas recrystallized from isopropanol

Sources & evidence

ORD record
ord-1961059a66c541b6a4c4c303a94fa72c
Source dataset
uspto-grants-1986_07
Patent number
US04599347

Reaction notes

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