Hydrochloric Acid → HCID 19096896, compound

HRID 487004Notes

Reaction equation

HRID 487004 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 XLVII (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. Elemental analysis of the product indicated the following:

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-862fa2eeecf549498a3eeed2a766c42c
Source dataset
uspto-grants-1994_03
Patent number
US05292937

Reaction notes

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