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

HRID 1580835

Reaction equation

HRID 1580835 reaction equation
[Cl:1][C:2]1[CH:20]=[CH:19][CH:18]=[C:17]([Cl:21])[C:3]=1[C:4]([NH:6][C:7]([NH:9][C:10]1[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][CH:11]=1)=[O:8])=[O:5].[OH-].[K+].CI.[CH3:26][O:27][CH2:28]Cl>CN(C)C=O>[Cl:1][C:2]1[CH:20]=[CH:19][CH:18]=[C:17]([Cl:21])[C:3]=1[C:4]([N:6]([CH2:26][O:27][CH3:28])[C:7]([NH:9][C:10]1[CH:11]=[CH:12][C:13]([Cl:16])=[CH:14][CH:15]=1)=[O:8])=[O:5]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 7864Chloromethyl Methyl EtherHCID 14797Potassium HydroxideHCID 923002,6-dichloro-N-(((4-chlorophenyl)amino)carbonyl)benzamide

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

10.3 g of N-(2,6-dichlorobenzoyl)-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-277ceea740284e078a68a7b03259edee
Source dataset
uspto-grants-1976_01
Patent number
US03933908

Linked notes

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