2-Chlorobenzoyl chloride → HCID 13361933, compound

HRID 255475Notes

Reaction equation

HRID 255475 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]([OH:16])([C:13]([NH2:15])=[O:14])[C:10]([NH2:12])=[O:11])[CH:5]=[CH:6][C:7]=1[Cl:8].[Cl:17][C:18]1[CH:26]=[CH:25][CH:24]=[CH:23][C:19]=1[C:20](Cl)=[O:21]>N1C=CC=CC=1.C(OCC)(=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]([O:16][C:20](=[O:21])[C:19]2[CH:23]=[CH:24][CH:25]=[CH:26][C:18]=2[Cl:17])([C:10]([NH2:12])=[O:11])[C:13]([NH2:15])=[O:14])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

5

Reactant 2

HCID 691102-Chlorobenzoyl chlorideHCID 158916Propanediamide, 2-(3,4-dichlorophenyl)-2-hydroxy-

Product 1

HCID 13361933HCID 13361933, compoundYield 33.1%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8857Ethyl AcetateSolvent

Procedure

26.3 g of 3,4-dichlorophenylhydroxymalonic acid diamide were dissolved in 50 ml of pyridine, and 17.1 g of o-chlorobenzoyl chloride were added at below 30° C. After one hour, the mixture was stirred into cold 1NCl, the precipitate was taken up in ethyl acetate, the mixture was extracted by shaking and the extract was worked up. 26.5 g of crude product remained, and were recrystallised from 400 ml of ethanol. 13 g of pure 3,4-dichlorophenyl-(2-chlorobenzoyloxy)-malonic acid diamide of melting point 220° C. were obtained.

Workup

  1. extractionthe mixture was extracted
  2. stirringby shaking
  3. customwere recrystallised from 400 ml of ethanol

Sources & evidence

ORD record
ord-906644ff2c904493af58f9580868a666
Source dataset
uspto-grants-1987_10
Patent number
US04698333

Reaction notes

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