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Water → 1-(4-Chlorobenzyl)-1,3-dimethyl-3-[2-methyl-1-(4-trifluoromethyl-pyrimidin-5-yl)-propyl]-urea

HRID 393147
Notes
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Reaction equation

HRID 393147 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([CH2:6][NH:7][CH3:8])=[CH:4][CH:3]=1.[CH3:11][N:12]([CH:16]([C:20]1[C:21]([C:26]([F:29])([F:28])[F:27])=[N:22][CH:23]=[N:24][CH:25]=1)[CH:17]([CH3:19])[CH3:18])[C:13](Cl)=[O:14].O>N1C=CC=CC=1>[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([CH2:6][N:7]([CH3:8])[C:13]([N:12]([CH3:11])[CH:16]([C:20]2[C:21]([C:26]([F:29])([F:28])[F:27])=[N:22][CH:23]=[N:24][CH:25]=2)[CH:17]([CH3:19])[CH3:18])=[O:14])=[CH:4][CH:3]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 962WaterHCID 66905Benzenemethanamine, 4-chloro-N-methyl-HCID 22648762N-methyl-N-(2-methyl-1-(4-trifluoromethyl-pyrimidin-5-yl)-propyl]-carbamoyl chloride

Product 1

HCID 226487481-(4-Chlorobenzyl)-1,3-dimethyl-3-[2-methyl-1-(4-trifluoromethyl-pyrimidin-5-yl)-propyl]-ureaYield 53%

Reagents, catalysts & solvents 1

HCID 1049
Pyridine
Solvent

Procedure

0.16 g (1.0 mmol) of (4-chlorobenzyl)-methylamine was dissolved in 30 ml of pyridine, and 0.3 g (1.0 mmol) of N-methyl-N-(2-methyl-1-(4-trifluoromethyl-pyrimidin-5-yl)-propyl]-carbamoyl chloride was dropwise added, followed by stirring at room temperature for 10 hours. To the reaction solution, 50 ml of water was added, followed by extraction with diethyl ether. The obtained organic phase was washed twice with 30 ml of a dilute citric acid aqueous solution, followed by drying over anhydrous magnesium sulfate. Diethyl ether was distilled off under reduced pressure, and the obtained crude product was purified by silica gel chromatography (developing solvent/n-hexane:ethyl acetate=8:1 to 3:1) to obtain 0.22 g (yield: 52%) of 1-(4-chlorobenzyl)-1,3-dimethyl-3-[2-methyl-1-(4-trifluoromethyl-pyrimidin-5-yl)-propyl]-urea as colorless crystals (melting point: 95-98° C.).

Workup

  1. extractionfollowed by extraction with diethyl ether
  2. washThe obtained organic phase was washed twice with 30 ml of a dilute citric acid aqueous solution
  3. dry with materialby drying over anhydrous magnesium sulfate
  4. distillationDiethyl ether was distilled off under reduced pressure
  5. customthe obtained crude product
  6. customwas purified by silica gel chromatography (developing solvent/n-hexane:ethyl acetate=8:1 to 3:1)

Sources & evidence

ORD record
ord-b78e4978d4cc488ba0ae97f5638edd15
Source dataset
uspto-grants-2004_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06806230B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes