Dicyclohexylcarbodiimide → HCID 178477304, compound

HRID 1275469Notes

Reaction equation

HRID 1275469 reaction equation
[CH2:1]([S:3][CH:4]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([C:15]([OH:17])=O)[C:12]=2[CH3:14])[S:7](=[O:19])(=[O:18])[CH2:6][CH2:5]1)[CH3:2].[CH2:20]([N:22]1[C:26]([OH:27])=[CH:25][CH:24]=[N:23]1)[CH3:21].C1(N=C=NC2CCCCC2)CCCCC1.C(=O)([O-])[O-].[K+].[K+]>C(O)(CC)(C)C>[CH2:1]([S:3][CH:4]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([C:15]([C:25]3[CH:24]=[N:23][N:22]([CH2:20][CH3:21])[C:26]=3[OH:27])=[O:17])[C:12]=2[CH3:14])[S:7](=[O:19])(=[O:18])[CH2:6][CH2:5]1)[CH3:2]

Participants

6

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 11430Potassium CarbonateHCID 22118456HCID 22118456, compoundHCID 178418331HCID 178418331, compound

Product 1

HCID 178477304HCID 178477304, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 64052-Methyl-2-butanolSolvent

Procedure

0.51 Gram (1.7 mmol) of 4-ethylthio-5-methyl-6-carboxythiochroman-1,1-dioxide was dissolved in 5 ml of t-amyl alcohol, and 0.22 g (2.0 mmol, 1.2 eq.) of 1-ethyl-5-hydroxypyrazole and 0.42 g (2.0 mmol, 1.2 eq.) of N,N'-dicyclohexylcarbodiimide were added. The mixture was stirred at room temperature for 3 hours, and then 0.18 g (1.3 mmol) of potassium carbonate was added. The mixture was heated at 80° C. for 8 hours. After the completion of the reaction, the solvent was distilled off. The remaining oil was dissolved in ethyl acetate and product was extracted with a 5 wt % sodium hydrogencarbonate aqueous solution. 2N Hydrochloric acid was added to the resultant aqueous solution to adjust a pH of 1, and the mixture was extracted with ethyl acetate. An organic layer was washed with a saturated sodium chloride aqueous solution and dried over anhydrous sodium sulfate, and the solvent was distilled off to give 0.5 g (75%) of 4-ethylthio-5-methyl-6-(1-ethyl-5-hydroxypyrazol-4-yl)carbonylthiochroman-1,1-dioxide.

Workup

  1. temperatureThe mixture was heated at 80° C. for 8 hours
  2. customAfter the completion of the reaction
  3. distillationthe solvent was distilled off
  4. dissolutionThe remaining oil was dissolved in ethyl acetate
  5. extractionproduct was extracted with a 5 wt % sodium hydrogencarbonate aqueous solution
  6. addition2N Hydrochloric acid was added to the resultant aqueous solution
  7. extractionthe mixture was extracted with ethyl acetate
  8. washAn organic layer was washed with a saturated sodium chloride aqueous solution
  9. dry with materialdried over anhydrous sodium sulfate
  10. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-029e7e2348174709ba002fd45dff55ef
Source dataset
uspto-grants-2000_12
Patent number
US06159904

Reaction notes

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