N,N'-Dicyclohexylurea → 4-Ethylthio-5-methyl-6-(1-ethylpyrazol-5-yl)oxycarbonyl-8-chlorothiochroman

HRID 1275471Notes

Reaction equation

HRID 1275471 reaction equation
[CH2:1]([S:3][CH:4]1[C:13]2[C:8](=[C:9]([Cl:18])[CH:10]=[C:11]([C:15]([OH:17])=[O:16])[C:12]=2[CH3:14])[S:7][CH2:6][CH2:5]1)[CH3:2].[CH2:19]([N:21]1[C:25](O)=[CH:24][CH:23]=[N:22]1)[CH3:20].C1(N=C=NC2CCCCC2)CCCCC1.C1(NC(NC2CCCCC2)=O)CCCCC1>C(O)(CC)(C)C.CCCCCC.C(OCC)(=O)C>[CH2:1]([S:3][CH:4]1[C:13]2[C:8](=[C:9]([Cl:18])[CH:10]=[C:11]([C:15]([O:17][C:25]3[N:21]([CH2:19][CH3:20])[N:22]=[CH:23][CH:24]=3)=[O:16])[C:12]=2[CH3:14])[S:7][CH2:6][CH2:5]1)[CH3:2]

Participants

8

Reactant 4

HCID 4277N,N'-DicyclohexylureaHCID 10868DicyclohexylcarbodiimideHCID 221184154-Ethylthio-5-methyl-6-carboxy-8-chlorothiochromanHCID 178418331HCID 178418331, compound

Product 1

HCID 221183934-Ethylthio-5-methyl-6-(1-ethylpyrazol-5-yl)oxycarbonyl-8-chlorothiochromanYield 106.9%

Reagents, catalysts & solvents 3

HCID 64052-Methyl-2-butanolSolventHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

1.0 Gram (3.3 mmol) of 4-ethylthio-5-methyl-6-carboxy-8-chlorothiochroman was dissolved in 5 ml of t-amyl alcohol, and 0.45 g (4.0 mmol, 1.2 eq.) of 1-ethyl-5-hydroxypyrazole and 0.83 g (4.0 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, ethyl acetate and hexane were added, and liberated N,N'-dicyclohexylurea was filtered off. The filtrate was concentrated and purified by column chromatography (silica gel/hexane+ethyl acetate=5:1) to give 1.4 g (yield 100%) of 4-ethylthio-5-methyl-6-(1-ethylpyrazol-5-yl)oxycarbonyl-8-chlorothiochroman.

Workup

  1. additionwere added
  2. filtrationwas filtered off
  3. concentrationThe filtrate was concentrated
  4. custompurified by column chromatography (silica gel/hexane+ethyl acetate=5:1)

Sources & evidence

ORD record
ord-705e8cc1da8d4e1f80bef8834a0e5663
Source dataset
uspto-grants-2000_12
Patent number
US06159904

Reaction notes

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