(4-Aminophenoxy)benzene → HCID 4548294, compound

HRID 2109617Notes

Reaction equation

HRID 2109617 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.CCOC(C)=O>C(Cl)Cl>[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 4

HCID 8764(4-Aminophenoxy)benzeneHCID 8857Ethyl AcetateHCID 81531DiisopropylethylamineHCID 27745412-Chloronicotinoyl chloride

Product 1

HCID 4548294HCID 4548294, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-Chloronicotinoyl chloride (9.15 g, 0.052 mol) was added to a stirred solution of 4-phenoxyaniline (10.00 g, 0.054 mol) and DIEA (10.00 ml, 0.057 mol) in CH2Cl2 (100 ml) at RT. The mixture stirred for 48 h before removal of solvent under reduced pressure. The resulting residue was dissolved 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 leave 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-1eeeff5f9d7d46b6a23b31b5a0f6b96c
Source dataset
uspto-grants-2009_04
Patent number
US07514564B2

Reaction notes

Loading…