Dimethyl Sulfoxide → HCID 15137713, compound

HRID 359992Notes

Reaction equation

HRID 359992 reaction equation
[CH2:1]([C:5]1[CH:10]=[CH:9][C:8]([CH2:11][N:12]([CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29]OS(C)(=O)=O)[C:13]([NH:15][C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][C:17]=2[CH3:23])=[O:14])=[CH:7][CH:6]=1)[CH2:2][CH2:3][CH3:4].[Cl-:35].[K+].CS(C)=O>O>[CH2:1]([C:5]1[CH:10]=[CH:9][C:8]([CH2:11][N:12]([CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][Cl:35])[C:13]([NH:15][C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][C:17]=2[CH3:23])=[O:14])=[CH:7][CH:6]=1)[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 4873Potassium ChlorideHCID 15137707HCID 15137707, compound

Product 1

HCID 15137713HCID 15137713, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 2.0 g of 1-[(4-butylphenyl)methyl]-3-(4-chloro-2-methylphenyl)-1-[6-[(methylsulfonyl)oxy]hexyl]urea, 0.74 g of potassium chloride, and 3.0 ml of dimethyl sulfoxide was heated at an oil bath temperature of 60°-80° C. for 16 hours. The mixture was diluted with water and extracted with dichloromethane. The organic layer was washed with three 40 ml portions of brine, dried over anhydrous magnesium sulfate and filtered. The filtrate was evaporated in vacuo to yield 1.5 g of a brown oil. The oil was purified by chromatography to yield 1.5 g of the desired product as a light yellow oil in 86% yield.

Workup

  1. temperaturewas heated at an oil bath temperature of 60°-80° C. for 16 hours
  2. extractionextracted with dichloromethane
  3. washThe organic layer was washed with three 40 ml portions of brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customThe filtrate was evaporated in vacuo

Sources & evidence

ORD record
ord-6452e1a135704951b4840f9571ff2937
Source dataset
uspto-grants-1991_03
Patent number
US05003106

Reaction notes

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