Dicyclohexylcarbodiimide → 8-Chloro-6-(1-ethylpyrazol-5-yl)oxycarbonyl-4,4-ethylenedioxy-5-methylthiochroman-1,1-dioxide

HRID 1275444Notes

Reaction equation

HRID 1275444 reaction equation
[C:1]([C:4]1[C:5]([CH3:21])=[C:6]2[C:11](=[C:12]([Cl:14])[CH:13]=1)[S:10](=[O:16])(=[O:15])[CH2:9][CH2:8][C:7]12[O:20][CH2:19][CH2:18][O:17]1)([OH:3])=[O:2].[CH2:22]([N:24]1[C:28](O)=[CH:27][CH:26]=[N:25]1)[CH3:23].C1(N=C=NC2CCCCC2)CCCCC1>C(Cl)Cl>[Cl:14][C:12]1[CH:13]=[C:4]([C:1]([O:3][C:28]2[N:24]([CH2:22][CH3:23])[N:25]=[CH:26][CH:27]=2)=[O:2])[C:5]([CH3:21])=[C:6]2[C:11]=1[S:10](=[O:16])(=[O:15])[CH2:9][CH2:8][C:7]12[O:20][CH2:19][CH2:18][O:17]1

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 22118398HCID 22118398, compoundHCID 178418331HCID 178418331, compound

Product 1

HCID 221184118-Chloro-6-(1-ethylpyrazol-5-yl)oxycarbonyl-4,4-ethylenedioxy-5-methylthiochroman-1,1-dioxideYield 81%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

0.92 Gram (2.8 mmol) of 6-carboxy-8-chloro-4,4-ethylenedioxy-5-methylthiochroman-1,1-dioxide was dissolved in 10 ml of methylene chloride, and 0.34 g (1.1 eq., 3.0 mmol) of 1-ethyl-5-hydroxypyrazole and 0.63 g (1.1 eq., 3.1 mmol) of N,N'-dicyclohexylcarbodiimide were added. The mixture was stirred at room temperature for 5 hours. Then, an insoluble substance was removed by filtration, and the filtrate was washed with a saturated sodium chloride aqueous solution and dried over anhydrous sodium sulfate. The solvent was distilled off to give 0.96 g (yield 81%) of 8-chloro-6-(1-ethylpyrazol-5-yl)oxycarbonyl-4,4-ethylenedioxy-5-methylthiochroman-1,1-dioxide.

Workup

  1. customThen, an insoluble substance was removed by filtration
  2. washthe filtrate was washed with a saturated sodium chloride aqueous solution
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationThe solvent was distilled off

Sources & evidence

ORD record
ord-a95d7ae3fa564e13bcd5f7a5964d5395
Source dataset
uspto-grants-2000_12
Patent number
US06159904

Reaction notes

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