(4-Aminophenoxy)benzene → HCID 4548294, compound

HRID 557381Notes

Reaction equation

HRID 557381 reaction equation
[Cl:1][C:2]1[N:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.ClC(OCC)=O.[O:17]([C:24]1[CH:30]=[CH:29][C:27]([NH2:28])=[CH:26][CH:25]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>C1COCC1>[Cl:1][C:2]1[C:3]([C:4]([NH:28][C:27]2[CH:26]=[CH:25][C:24]([O:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[CH:30][CH:29]=2)=[O:6])=[CH:7][CH:8]=[CH:9][N:10]=1

Participants

5

Reactant 3

HCID 8764(4-Aminophenoxy)benzeneHCID 10928Ethyl chloroformateHCID 762582-Chloronicotinic acid

Product 1

HCID 4548294HCID 4548294, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-Chloronicotinic acid (0.78 g, 5.0 mmol) and TEA (1.6 ml, 10.0 mmol) were added to anhydrous THF (50 ml) under a N2 atmosphere at 0° C. After stirring for 5 min, ethyl chloroformate (0.54 g, 5.0 mmol) was added dropwise and the mixture gradually came to RT over a period of 1 h. 4-Phenoxyaniline (0.83 g, 5.0 mmol) was added and the mixture was stirred for 14 h. The mixture was partitioned between H2O and EtOAc. The aqueous layer was extracted two additional times with EtOAc (50 ml). The combined organic layers were then washed with brine, dried over Na2SO4, and evaporated. The resulting brown oil was used directly in the subsequent reaction without further purification. MS m/z: 325 (M+1). Calc'd for C18H13ClN2O2: 324.07.

Workup

  1. waitthe mixture gradually came to RT over a period of 1 h
  2. stirringthe mixture was stirred for 14 h
  3. customThe mixture was partitioned between H2O and EtOAc
  4. extractionThe aqueous layer was extracted two additional times with EtOAc (50 ml)
  5. washThe combined organic layers were then washed with brine
  6. dry with materialdried over Na2SO4
  7. customevaporated
  8. customThe resulting brown oil was used directly in the subsequent reaction without further purification

Sources & evidence

ORD record
ord-c1903880e91a4fd99f6c7297b9079934
Source dataset
uspto-grants-2011_11
Patent number
US08058445B2

Reaction notes

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