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Ethylenediamine → HCID 10390732, compound

HRID 1821963
Notes
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Reaction equation

HRID 1821963 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([O:8][CH2:9][CH:10]=[C:11]([Cl:13])[Cl:12])[CH:5]=[C:4]([Cl:14])[C:3]=1[O:15][CH2:16][CH2:17][CH2:18][O:19][C:20]1[CH:25]=[CH:24][C:23](I)=[CH:22][CH:21]=1.[NH:27]1[CH:31]=[CH:30][CH:29]=[CH:28]1.C(N)CN.[O-]P(OP(OP([O-])([O-])=O)([O-])=O)(=O)[O-].[K+].[K+].[K+].[K+].[K+]>O1CCOCC1.C(OCC)(=O)C.[Cu]I>[Cl:1][C:2]1[CH:7]=[C:6]([O:8][CH2:9][CH:10]=[C:11]([Cl:13])[Cl:12])[CH:5]=[C:4]([Cl:14])[C:3]=1[O:15][CH2:16][CH2:17][CH2:18][O:19][C:20]1[CH:25]=[CH:24][C:23]([N:27]2[CH:31]=[CH:30][CH:29]=[CH:28]2)=[CH:22][CH:21]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 3301EthylenediamineHCID 8027PyrroleHCID 61695Pentapotassium TriphosphateHCID 18442679HCID 18442679, compound

Product 1

HCID 10390732HCID 10390732, compound

Reagents, catalysts & solvents 3

HCID 24350
Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)
Catalyst
HCID 8857Ethyl AcetateSolvent
HCID 312751,4-DioxaneSolvent

Procedure

200 mg of 1,3-dichloro-5-(3,3-dichloro-allyloxy)-2-[3-(4-iodo-phenoxy)-propoxy]-benzene, 29 mg of pyrrole, 6.9 mg of copper(I) iodide, 2.2 mg of ethylenediamine and 155 mg of potassium triphosphate are stirred for 24 hours at 110° C. in 4 ml of dioxane. The reaction mixture is diluted with ethyl acetate and filtered. Concentration and purification over silica gel yield the title compound (compound 1.1).

Workup

  1. filtrationfiltered
  2. concentrationConcentration and purification over silica gel

Sources & evidence

ORD record
ord-8e6e362e26fb42629792730ee4e22fd8
Source dataset
uspto-grants-2009_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07608631B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes