Chloramben → HCID 178467924, compound

HRID 2418948Notes

Reaction equation

HRID 2418948 reaction equation
[CH3:1][C:2]([C:4]([C:9]([CH3:11])=[O:10])=[CH:5]OCC)=[O:3].[NH2:12][C:13]1[C:14]([Cl:23])=[C:15]([CH:19]=[C:20]([Cl:22])[CH:21]=1)[C:16]([OH:18])=[O:17]>CCOCC>[CH3:11][C:9]([C:4]([C:2]([CH3:1])=[O:3])=[CH:5][NH:12][C:13]1[C:14]([Cl:23])=[C:15]([CH:19]=[C:20]([Cl:22])[CH:21]=1)[C:16]([OH:18])=[O:17])=[O:10]

Participants

4

Reactant 2

HCID 8630ChlorambenHCID 2404183-(Ethoxymethylene)pentane-2,4-dione

Product 1

HCID 178467924HCID 178467924, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

9.35 g (0.06 mole) of methyl 1-methylcarbonyl-2-ethoxyvinyl ketone were added dropwise to a suspension of 10.3 g (0.05 mole) of 3-amino-2,5-dichlorobenzoic acid in 40 ml of ether. The mixture was stirred for a further 5 hours at room temperature and the precipitate was then filtered off and washed with acetonitrile. 12 g (76% of theory) of 3-[2,2-bis-(methylcarbonyl)-vinylamino]-2,5-dichlorobenzoic acid were obtained in the form of colourless crystals of melting point 244°-246° C.

Workup

  1. filtrationthe precipitate was then filtered off
  2. washwashed with acetonitrile

Sources & evidence

ORD record
ord-7879e81ac69a4340bf6b746e8861f65c
Source dataset
uspto-grants-1978_08
Patent number
US04104049

Reaction notes

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