Dicyclohexylcarbodiimide → HCID 178463098, compound

HRID 1275474Notes

Reaction equation

HRID 1275474 reaction equation
[OH:1][CH:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:13]([OH:15])=O)[C:10]=2[CH3:12])[S:5](=[O:17])(=[O:16])[CH2:4][CH2:3]1.[CH2:18]([N:20]1[C:24]([OH:25])=[CH:23][CH:22]=[N:21]1)[CH3:19].C1(N=C=NC2CCCCC2)CCCCC1.C(=O)([O-])[O-].[K+].[K+]>C(O)(CC)(C)C>[OH:1][CH:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:13]([C:23]3[CH:22]=[N:21][N:20]([CH2:18][CH3:19])[C:24]=3[OH:25])=[O:15])[C:10]=2[CH3:12])[S:5](=[O:17])(=[O:16])[CH2:4][CH2:3]1

Participants

6

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 11430Potassium CarbonateHCID 23450690HCID 23450690, compoundHCID 178418331HCID 178418331, compound

Product 1

HCID 178463098HCID 178463098, compoundYield 73.2%

Reagents, catalysts & solvents 1

HCID 64052-Methyl-2-butanolSolvent

Procedure

2.0 Grams (7.8 mmol) of 4-hydroxy-6-carboxy-5-methylthiochroman-1,1-dioxide was dissolved in 10 ml of t-amyl alcohol, and 1.0 g (8.6 mmol, 1.1 eq.) of 1-ethyl-5-hydroxypyrazole and 1.8 g (8.6 mmol, 1.1 eq.) of N,N'-dicyclohexylcarbodiimide were added. The mixture was stirred at room temperature for 3 hours. Then, 0.8 g (5.9 mmol) of potassium carbonate was added. The mixture was heated at 80° C. for 6 hours. After the completion of the reaction, the solvent was distilled off. The remaining oil was dissolved in ethyl acetate, and end product was extracted with a 5 wt % sodium hydrogencarbonate aqueous solution. The resultant aqueous solution was adjusted to a pH of 1 in an ice bath by adding 2N hydrochloric acid, and 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 2.0 g (yield 73%) of 4-hydroxy-5-methyl-6-(1-ethyl-5-hydroxypyrazol-4-yl)carbonylthiochroman-1,1-dioxide.

Workup

  1. temperatureThe mixture was heated at 80° C. for 6 hours
  2. customAfter the completion of the reaction
  3. distillationthe solvent was distilled off
  4. dissolutionThe remaining oil was dissolved in ethyl acetate
  5. extractionend product was extracted with a 5 wt % sodium hydrogencarbonate aqueous solution
  6. customThe resultant aqueous solution was adjusted to a pH of 1 in an ice bath
  7. additionby adding 2N hydrochloric acid
  8. extractionextracted with ethyl acetate
  9. washAn organic layer was washed with a saturated sodium chloride aqueous solution
  10. dry with materialdried over anhydrous sodium sulfate
  11. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-029d52279d184d12a2a79435aea25567
Source dataset
uspto-grants-2000_12
Patent number
US06159904

Reaction notes

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