1,1-Dimethoxyethane → Methyl 3-[(3,5-dichlorophenyl)amino]-2-methoxy-3-thioxopropanoate

HRID 893232Notes

Reaction equation

HRID 893232 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10](=O)[CH:11]([O:16][CH3:17])[C:12]([O:14][CH3:15])=[O:13])[CH:5]=[C:6]([Cl:8])[CH:7]=1.COC1C=CC(P2(=S)SP(=S)(C3C=CC(OC)=CC=3)[S:28]2)=CC=1.COC(OC)C>>[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10](=[S:28])[CH:11]([O:16][CH3:17])[C:12]([O:14][CH3:15])=[O:13])[CH:5]=[C:6]([Cl:8])[CH:7]=1

Participants

4

Reactant 3

HCID 107951,1-DimethoxyethaneHCID 87949Lawesson's reagentHCID 19096902HCID 19096902, compound2×

Product 1

HCID 19096897Methyl 3-[(3,5-dichlorophenyl)amino]-2-methoxy-3-thioxopropanoateYield 116.7%

Procedure

A mixture of 3.50 grams (0.01 mole) of methyl 3-[(3,5-dichlorophenyl)amino]-2-methoxy-3-oxopropanoate (Compound 233, Example LXX), 2.42 grams (0.006 mole) of 2,4-bis(4-methoxyphenyl)-1,3-dithia-2,4-diphosphetane-2,4-disulfide and 35 milliliters of anhydrous 1,1-dimethoxyethane was stirred at room temperature for a period of about 20 hours after which stirring was continued with testing at 55° C. for a 168-hour interval. Solvent was removed from the reaction mixture under reduced pressure and the residue worked up by flash column chromatography to give 2.31 grams (0.007 mole) of methyl 3-[(3,5-dichloro-phenyl)amino]-2-methoxy-3-thioxopropanoate having a melting point of 144° C.-147° C.

Workup

  1. stirringstirring
  2. waitwas continued with testing at 55° C. for a 168-hour
  3. customSolvent was removed from the reaction mixture under reduced pressure

Sources & evidence

ORD record
ord-8dd4fed8c2e346c7b66ebb976978488d
Source dataset
uspto-grants-1992_06
Patent number
US05123951

Reaction notes

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