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Dimethylformamide → propargyl N-methoxy-2,4-dichlorobenzimidate

HRID 3405
Notes
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Reaction equation

HRID 3405 reaction equation
[CH3:1][O:2][NH:3][C:4](=[O:13])[C:5]1[CH:10]=[CH:9][C:8]([Cl:11])=[CH:7][C:6]=1[Cl:12].C(=O)([O-])[O-].[K+].[K+].[CH2:20](Br)[C:21]#[CH:22].CN(C)C=O>O>[CH3:1][O:2][N:3]=[C:4]([O:13][CH2:22][C:21]#[CH:20])[C:5]1[CH:10]=[CH:9][C:8]([Cl:11])=[CH:7][C:6]=1[Cl:12]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 7842Propargyl bromideHCID 11430Potassium CarbonateHCID 189350352,4-dichloro-N-methoxybenzamide

Product 1

HCID 53654798propargyl N-methoxy-2,4-dichlorobenzimidateYield 29.8%

Reagents, catalysts & solvents 1

HCID 962
Water
Solvent

Procedure

1.0 g of N-methoxy-2,4-dichlorobenzamide, 0.75 g of potassium carbonate and 0.65 g of propargyl bromide were added to 10 ml of N,N-dimethylformamide, and the mixture was stirred for 3 hours. After completion of the reaction, water was added to the reaction solution, and the mixture was extracted with ethyl acetate. The extract was dried, concentrated and purified by silica gel column chromatography to obtain 0.35 g of propargyl N-methoxy-2,4-dichlorobenzimidate.

Workup

  1. additionwas added to the reaction solution
  2. extractionthe mixture was extracted with ethyl acetate
  3. customThe extract was dried
  4. concentrationconcentrated
  5. custompurified by silica gel column chromatography

Sources & evidence

ORD record
ord-bc47ddbc82764811b755545cf676a4fc
Source dataset
uspto-grants-1998_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05733935

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes