Hydrochloric Acid → HCID 19096896, compound

HRID 893215Notes

Reaction equation

HRID 893215 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:20])[C:10](=S(C)(C)=O)[C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:4][CH:3]=1.[ClH:21]>C(Cl)(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:20])[CH:10]([Cl:21])[C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86745931HCID 86745931, compound

Product 1

HCID 19096896HCID 19096896, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A solution of 1.5 grams (0.05 mole) of ethyl 3-[(4-chlorophenyl)amino]-2-(dimethyloxosulfuranylidene)-3-oxopropanoate prepared in Example XLXII (Compound 205) in 25 milliliters of chloroform was stirred at room temperature for two hours while passing in a flow of anhydrous hydrogen chloride. After ceasing the gas feed the solution was stirred at ambient temperature for about 64 hours after which the solvent was removed under reduced pressure. Flash chromatography of the residue eluting with hexane-ethyl acetate (7:3), gave a white solid which was recrystallized from ethyl acetate-hexane to give 0.20 gram (0.001 mole) of ethyl 3-[(4-chlorophenyl)amino]-2-chloro-3-oxopropanoate having a melting point of 104° C.-105° C.

Workup

  1. stirringwas stirred at ambient temperature for about 64 hours after which the solvent
  2. customwas removed under reduced pressure
  3. washFlash chromatography of the residue eluting with hexane-ethyl acetate (7:3)
  4. customgave a white solid which
  5. customwas recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-9078a9763d3a4374935da9e33935149b
Source dataset
uspto-grants-1992_06
Patent number
US05123951

Reaction notes

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