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Methyl iodide → N-(2,6-dichlorobenzoyl)-N-(methoxymethyl)-N'-(4-chlorophenyl)-urea

HRID 1762450
Notes
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Reaction equation

HRID 1762450 reaction equation
[Cl:1][C:2]1[CH:19]=[CH:18][CH:17]=[C:16]([Cl:20])[C:3]=1[CH2:4][NH:5][C:6]([NH:8][C:9]1[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][CH:10]=1)=[O:7].[OH-:21].[K+].CI.[CH3:25][O:26][CH2:27]Cl>CN(C)C=O>[Cl:1][C:2]1[CH:19]=[CH:18][CH:17]=[C:16]([Cl:20])[C:3]=1[C:4]([N:5]([CH2:25][O:26][CH3:27])[C:6]([NH:8][C:9]1[CH:10]=[CH:11][C:12]([Cl:15])=[CH:13][CH:14]=1)=[O:7])=[O:21]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 7864Chloromethyl Methyl EtherHCID 14797Potassium HydroxideHCID 20041301HCID 20041301, compound

Product 1

HCID 19006383N-(2,6-dichlorobenzoyl)-N-(methoxymethyl)-N'-(4-chlorophenyl)-urea

Reagents, catalysts & solvents 1

HCID 6228
Dimethylformamide
Solvent

Procedure

10.3 g of N-(2,6-dichlorobenzyl)-N'-(4-chlorophenyl)-urea and 1.88 g of powdered potassium hydroxide (90%) are dissolved 40 ml of dimethyl formamide, after which 4.7 g of methyl iodide are added drop by drop to the clear solution. The resulting reaction is exothermic. After stirring for two hours the solution is diluted with ice water and the solid substance is isolated. Yield 10.3 g. Melting point 124°-126° C. In a completely similar manner but using methoxymethylchloride instead of methyliodide, N-(2,6-dichlorobenzoyl)-N-(methoxymethyl)-N'-(4-chlorophenyl)-urea is produced, Melting point 121.5°-122.5° C.

Workup

  1. customThe resulting reaction
  2. customthe solid substance is isolated

Sources & evidence

ORD record
ord-2e78d63025544cafb0d60f96a25868c6
Source dataset
uspto-grants-1989_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04833151

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes