Phosphorus oxychloride → HCID 117839343, compound

HRID 1477672Notes

Reaction equation

HRID 1477672 reaction equation
P(Cl)(Cl)(Cl)=O.[C:6]([O:9][CH2:10][C:11]([N:13]=[C:14]([NH:17][C:18]([NH:20][CH2:21][C:22]1[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=1)=[O:19])[S:15][CH3:16])=O)(=[O:8])[CH3:7]>C(Cl)(Cl)Cl>[C:6]([O:9][CH2:10][C:11]1[N:20]([CH2:21][C:22]2[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=2)[C:18](=[O:19])[N:17]=[C:14]([S:15][CH3:16])[N:13]=1)(=[O:8])[CH3:7]

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178503953HCID 178503953, compound

Product 1

HCID 117839343HCID 117839343, compoundYield 104.6%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Conditions

Temperature
80 °C

Procedure

A phosphorus oxychloride solution (3.0 mL) of 2-({[3-(4-chlorobenzyl)ureido](methylthio)methylene}amino)-2-oxoethyl acetate (201 mg, 0.616 mmol) synthesized in Reference Synthesis Example 327 was stirred at 80° C. for 3 hours. After completion of the reaction, the reaction solution was added to chloroform-saturated sodium bicarbonate aqueous solution and extraction from the resultant mixture with chloroform was performed. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=2/1→0/1) to obtain the title compound (219 mg, quantitative).

Workup

  1. customAfter completion of the reaction
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=2/1→0/1)

Sources & evidence

ORD record
ord-74bd08ad03f34a2cbc873f859cb53647
Source dataset
uspto-grants-2016_08
Patent number
US09403798B2

Reaction notes

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