Dimethylformamide → HCID 67771654, compound

HRID 440822Notes

Reaction equation

HRID 440822 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([O:12][C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=2)=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8].[C:20]1(=[O:26])[O:25][C:23](=O)[CH:22]=[CH:21]1.[CH2:27](Cl)Cl.CN(C)[CH:32]=[O:33]>CN(C)C1C=CN=CC=1.N1C=CC=CC=1>[C:7]([C:6]1[CH:11]=[C:2]([NH:1][C:32]([CH:21]([C:20]([OH:25])=[O:26])/[CH:22]=[CH:23]\[CH3:27])=[O:33])[CH:3]=[CH:4][C:5]=1[O:12][C:13]1[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=1)([O:9][CH3:10])=[O:8]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 6344DichloromethaneHCID 7923Maleic AnhydrideHCID 22404866HCID 22404866, compound

Product 1

HCID 67771654HCID 67771654, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Procedure

A.2. Reaction of methyl 5-amino-2-(4-chlorophenoxy)-benzoate with maleic anhydride in a solvent such as methylene chloride or dimethylformamide in the presence of pyridine or 4-dimethylaminopyridine gives (Z)-but-2-enedicarboxylic acid 3-carbomethoxy-4-(4-chloro-phenoxy)-phenylamide which is converted by saponification with aqueous sodium hydroxide or potassium hydroxide in water and a second solvent such as methanol, ethanol or acetonitrile into (Z)-but-2-enedicarboxylic acid 3-carboxy-4-(4-chloro-phenoxy)-phenylamide, melting point: 224°-226° C.

Sources & evidence

ORD record
ord-bf8662cbaca14860a2e80599e198b44d
Source dataset
uspto-grants-1996_05
Patent number
US05521160

Reaction notes

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