Water → HCID 15172251, compound

HRID 1195599Notes

Reaction equation

HRID 1195599 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:14]=[C:15]([Cl:17])[CH:16]=1)[O:5][NH:6][C:7](=[O:13])[N:8]([CH:10]([CH3:12])[CH3:11])[CH3:9].Cl[C:19]([O:21][CH3:22])=[O:20].O>O1CCCC1.N1C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]([CH:14]=[C:15]([Cl:17])[CH:16]=1)[O:5][N:6]([C:19]([O:21][CH3:22])=[O:20])[C:7](=[O:13])[N:8]([CH:10]([CH3:12])[CH3:11])[CH3:9]

Participants

6

Reactant 3

HCID 962WaterHCID 6586Methyl chloroformateHCID 13746451HCID 13746451, compound

Product 1

HCID 15172251HCID 15172251, compoundYield 44%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
25 °C

Procedure

In a mixed solvent of 20 ml of tetrahydrofuran and 1.9 ml of pyridine was dissolved 2.15 g (7.76 mmoles) of 3-(3,5-dichlorophenoxy)-1-isopropyl-1-methylurea, and then 10 ml of a tetrahydrofuran solution of 1.47 g (15.5 mmoles) of methyl chloroformate was added. The mixture was stirred at 25° C. for 2 hours. Water (100 ml) was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with a saturated aqueous sodium chloride solution, and dried over anhydrous magnesium sulfate. The ethyl acetate was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (eluting solvent: ethyl acetate/hexane) to give 1.14 g (yield 44 %) of the desired compound as the yellow crystals

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with a saturated aqueous sodium chloride solution
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe ethyl acetate was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (eluting solvent: ethyl acetate/hexane)

Sources & evidence

ORD record
ord-8d36fde13bb74a71888c6407ed2d23ef
Source dataset
uspto-grants-1992_05
Patent number
US05112385

Reaction notes

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