Acetic acid 10-acetoxymethyl-anthracen-9-ylmethyl ester → HCID 178429018, compound

HRID 1903144Notes

Reaction equation

HRID 1903144 reaction equation
C(O[C:4]([S-])=[S:5])C.[K+].[NH2:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][C:17]=1[NH2:18])[C:14]([CH3:20])([CH3:19])[C:13](=[O:21])[C:12]2([CH3:23])[CH3:22].CC(OCC1C2C(=CC=CC=2)C(COC(C)=O)=C2C=1C=CC=C2)=O>O>[SH:5][C:4]1[NH:18][C:17]2[CH:16]=[C:15]3[C:11](=[CH:10][C:9]=2[N:8]=1)[C:12]([CH3:23])([CH3:22])[C:13](=[O:21])[C:14]3([CH3:19])[CH3:20]

Participants

5

Reactant 3

HCID 613145Acetic acid 10-acetoxymethyl-anthracen-9-ylmethyl esterHCID 2735045Potassium ethylxanthateHCID 13343756HCID 13343756, compound

Product 1

HCID 178429018HCID 178429018, compoundYield 78.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
20 °C

Procedure

20 ml of water and 17.0 g of purified potassium ethylxanthate were added to 20.0 g of 5,6-diamino-1,1,3,3-tetramethyl-2-indanone, dissolved in 200 ml of alcohol, in a 750 ml sulfonation flask equipped with stirrer, thermometer, reflux condenser. The mixture was left to boil at reflux overnight, then diluted with 200 ml of water, neutralized with 20 ml of glacial acetic and stirred at 60°-70° C. for an additional 1 hour. After cooling to 20° C., the crystals were removed by filtration under suction. There were obtained 18.8 g (78.9% of theory) of 5,7-dihydro-2-mercapto-5,5,7,7-tetramethylindeno(5,6-d)-imidazol-6(1H)-one with a melting point above 300° C.

Workup

  1. customequipped with stirrer
  2. temperaturethermometer, reflux condenser
  3. waitThe mixture was left
  4. temperatureat reflux overnight
  5. customthe crystals were removed by filtration under suction

Sources & evidence

ORD record
ord-d6ea66b80ea34a8092a8d6304cc53d60
Source dataset
uspto-grants-1984_03
Patent number
US04435406

Reaction notes

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