Water → HCID 178463101, compound

HRID 2268003Notes

Reaction equation

HRID 2268003 reaction equation
[CH3:1][C:2]1[C:7]2[S:8](=[O:15])(=[O:14])[CH2:9][CH2:10][S:11](=[O:13])(=[O:12])[C:6]=2[CH:5]=[CH:4][C:3]=1[C:16](O)=[O:17].[CH2:19]([N:21]1[C:25]([OH:26])=[CH:24][CH:23]=[N:22]1)[CH3:20].C(=O)([O-])[O-].[K+].[K+].O>C(#N)C.C(=O)(O)[O-].[Na+]>[CH2:19]([N:21]1[C:25]([OH:26])=[C:24]([C:16]([C:3]2[CH:4]=[CH:5][C:6]3[S:11](=[O:13])(=[O:12])[CH2:10][CH2:9][S:8](=[O:15])(=[O:14])[C:7]=3[C:2]=2[CH3:1])=[O:17])[CH:23]=[N:22]1)[CH3:20]

Participants

7

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 18432365HCID 18432365, compoundHCID 178418331HCID 178418331, compound

Product 1

HCID 178463101HCID 178463101, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
20 °C

Procedure

5.0 g (0.017 mol) of 8-methyl-2,3-dihydro-1,1,4,4-tetraoxobenz[1,4]dithiin-7-carboxylic acid were dissolved in 50 ml of acetonitrile, and 1.93 g (0.017 mol) of 1-ethyl-5-hydroxypyrazole and 3.56 g (0.017 mol) of N,N-dicyclohexylcarbodiimide were added. The reaction mixture was stirred at 20° C. for one hour and then taken up in 100 ml of 2% sodium bicarbonate solution, the precipitate that formed was filtered off with suction and the filtrate was dried and concentrated. The remaining white solid (5.8 g) was subsequently dissolved in 15 ml of dioxane, 4.2 g (0.03 mol) of potassium carbonate were added and the mixture was heated under reflux for 3 hours. After cooling, water was added, the mixture was washed with ethyl acetate, the aqueous phase was adjusted to pH 3 using 2N hydrochloric acid and the precipitate was filtered off with suction, washed with water and dried.

Workup

  1. customthe precipitate that formed
  2. filtrationwas filtered off with suction
  3. customthe filtrate was dried
  4. concentrationconcentrated
  5. dissolutionThe remaining white solid (5.8 g) was subsequently dissolved in 15 ml of dioxane
  6. temperaturethe mixture was heated
  7. temperatureunder reflux for 3 hours
  8. temperatureAfter cooling
  9. washthe mixture was washed with ethyl acetate
  10. filtrationthe precipitate was filtered off with suction
  11. washwashed with water
  12. customdried

Sources & evidence

ORD record
ord-dbca6c41b18d45ac8ea2a4df8d056c63
Source dataset
uspto-grants-2001_12
Patent number
US06326333B1

Reaction notes

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