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1-Bromo-3-chlorobenzene → 1-(3-Chloro-phenyl)-3-(4-methyl-pyridin-3-yl)-imidazolidin-2-one

HRID 80115
Notes
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Reaction equation

HRID 80115 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][C:3]=1[N:8]1[CH2:12][CH2:11][NH:10][C:9]1=[O:13].Br[C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([Cl:21])[CH:16]=1.N[C@@H]1CCCC[C@H]1N.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>[Cu](I)I.O1CCOCC1>[Cl:21][C:17]1[CH:16]=[C:15]([N:10]2[CH2:11][CH2:12][N:8]([C:3]3[CH:4]=[N:5][CH:6]=[CH:7][C:2]=3[CH3:1])[C:9]2=[O:13])[CH:20]=[CH:19][CH:18]=1
ParticipantsProcedureSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 79281-Bromo-3-chlorobenzeneHCID 438061,2-Diaminocyclohexane, trans-HCID 62657Potassium Phosphate, TribasicHCID 596361701-(4-Methylpyridin-3-yl)imidazolidin-2-one

Product 1

HCID 498721531-(3-Chloro-phenyl)-3-(4-methyl-pyridin-3-yl)-imidazolidin-2-oneYield 59.25%

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalyst
HCID 312751,4-DioxaneSolvent

Procedure

Using the same reaction conditions as in Example 14, 1-(4-methyl-pyridin-3-yl)-imidazolidin-2-one (I-14b: 200 mg, 1.129 mmol) was reacted with 1-bromo-3-chloro-benzene (0.281 g, 1.471 mmol), 1,4-dioxane (20 mL), copper iodide (0.021 g, 0.110 mmol), trans-1,2-diamino cyclohexane (0.038 g, 0.333 mmol) and potassium phosphate (0.718 g, 3.386 mmol) to afford 192 mg of the product (59.25% yield).

Sources & evidence

ORD record
ord-d71274b8ea1f429d9e15181d06fc25ad
Source dataset
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
USRE045173E1

Reaction notes

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On this pageParticipantsProcedureSources & evidenceReaction notes