(4-Aminophenoxy)benzene → HCID 4548294, compound

HRID 887571Notes

Reaction equation

HRID 887571 reaction equation
[Cl:1][C:2]1[N:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4](Cl)=[O:5].[O:11]([C:18]1[CH:24]=[CH:23][C:21]([NH2:22])=[CH:20][CH:19]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.CCN(C(C)C)C(C)C>C(Cl)Cl.CCOC(C)=O>[Cl:1][C:2]1[C:3]([C:4]([NH:22][C:21]2[CH:20]=[CH:19][C:18]([O:11][C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[CH:24][CH:23]=2)=[O:5])=[CH:7][CH:8]=[CH:9][N:10]=1

Participants

6

Reactant 3

HCID 8764(4-Aminophenoxy)benzeneHCID 81531DiisopropylethylamineHCID 27745412-Chloronicotinoyl chloride

Product 1

HCID 4548294HCID 4548294, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

2-Chloronicotinoyl chloride (9.15 g, 0.052 mol) was added to a stirred solution of 4-phenoxyaniline (10 g, 0.054 mol) and DIEA (10 ml, 0.057 mol) in CH2Cl2 (100 ml) at RT. The mixture was stirred for 48 h before removal of solvent under reduced pressure. The resulting residue was dissolved in EtOAc and washed several times with saturated NaHCO3 aqueous solution and brine, respectively. The organic layer was dried over Na2SO4 and evaporated to leave a solid. This material was re-crystallized from EtOAc/Hexane mixture, followed by filtration and rinsing with Et2O to give the desired compound as a white solid. MS m/z: 325 (M+1); 323 (M−1).

Workup

  1. washwashed several times with saturated NaHCO3 aqueous solution and brine
  2. dry with materialThe organic layer was dried over Na2SO4
  3. customevaporated
  4. customto leave a solid
  5. customThis material was re-crystallized from EtOAc/Hexane mixture
  6. filtrationfollowed by filtration
  7. washrinsing with Et2O

Sources & evidence

ORD record
ord-47b36ef5880b458789f1a59661a0e0a7
Source dataset
uspto-grants-2012_08
Patent number
US08247430B2

Reaction notes

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