Dicyclohexylcarbodiimide → HCID 22118399, compound

HRID 1275472Notes

Reaction equation

HRID 1275472 reaction equation
[Cl:1][CH:2]1[CH:11]([Cl:12])[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:14]([OH:16])=[O:15])[C:9]=2[CH3:13])[S:4](=[O:18])(=[O:17])[CH2:3]1.[CH2:19]([N:21]1[C:25](O)=[CH:24][CH:23]=[N:22]1)[CH3:20].C1(N=C=NC2CCCCC2)CCCCC1>C(O)(CC)(C)C>[Cl:1][CH:2]1[CH:11]([Cl:12])[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:14]([O:16][C:25]3[N:21]([CH2:19][CH3:20])[N:22]=[CH:23][CH:24]=3)=[O:15])[C:9]=2[CH3:13])[S:4](=[O:17])(=[O:18])[CH2:3]1

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 22118368HCID 22118368, compoundHCID 178418331HCID 178418331, compound

Product 1

HCID 22118399HCID 22118399, compoundYield 96.2%

Reagents, catalysts & solvents 1

HCID 64052-Methyl-2-butanolSolvent

Procedure

1.5 Grams (4.9 mmol) of 3,4-dichloro-5-methyl-6-carboxythiochroman-1,1-dioxide was dissolved in 5 ml of t-amyl alcohol, and 1.1 g (5.3mmol, 1.2 eq.) of 1-ethyl-5-hydroxypyrazole and 1.1 g (5.3 mmol, 1.2 eq.) of N,N'-dicyclohexylcarbodiimide were added. The mixture was stirred at room temperature for 2.5 hours. After the completion of the reaction, the reaction mixture was extracted with ethyl acetate and hexane, and liberated N,N'-dicyclohexylurea was filtered off. An organic layer was concentrated under reduced pressure and purified by column chromatography (silica gel/ethyl acetate) to give 1.9 g (yield 95%) of 3,4-dichloro-5-methyl-6-(1-ethylpyrazol-5-yl)oxycarbonylthiochroman-1,1-dioxide.

Workup

  1. customAfter the completion of the reaction
  2. extractionthe reaction mixture was extracted with ethyl acetate and hexane
  3. filtrationwas filtered off
  4. concentrationAn organic layer was concentrated under reduced pressure
  5. custompurified by column chromatography (silica gel/ethyl acetate)

Sources & evidence

ORD record
ord-d49b2f10438a44b1b847841424854528
Source dataset
uspto-grants-2000_12
Patent number
US06159904

Reaction notes

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