4-Chloroaniline → Diisopropyl Ether

HRID 1509972Notes

Reaction equation

HRID 1509972 reaction equation
[C:1]([NH2:6])(=O)[CH:2]([CH3:4])[CH3:3].[N+:7]([C:10]1[CH:11]=[C:12]([NH2:19])[C:13](=[CH:17][CH:18]=1)[C:14]([OH:16])=O)([O-:9])=[O:8].[Cl:20][C:21]1[CH:27]=[CH:26][C:24](N)=[CH:23][CH:22]=1.P(Cl)(Cl)Cl>C1(C)C=CC=CC=1>[CH:21]([O:8][CH:2]([CH3:3])[CH3:4])([CH3:27])[CH3:22].[Cl:20][C:21]1[CH:27]=[CH:26][C:24]([N:6]2[C:14](=[O:16])[C:13]3[C:12](=[CH:11][C:10]([N+:7]([O-:9])=[O:8])=[CH:18][CH:17]=3)[N:19]=[C:1]2[CH:2]([CH3:4])[CH3:3])=[CH:23][CH:22]=1

Participants

6

Reactant 3

HCID 78124-ChloroanilineHCID 24387Phosphorus trichlorideHCID 67237480HCID 67237480, compound

Product 2

HCID 7914Diisopropyl EtherHCID 57625605HCID 57625605, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
150 °C

Procedure

A suspension of 4-nitroanthranilic acid isobutyramide (4 g, 15.8 mmol), 4-chloroaniline (2.2 g, 17.2 mmol) and phosphorus trichloride (5.6 mL) in toluene (150 mL) is heated to reflux (bath temperature for 150° C.) for 2 hours. The reaction mixture is allowed to cool to room temperature and then evaporated to dryness. The residue is partitioned between water and EtOAc and the aqueous phase is extracted (2×) with EtOAc. The combined organic phases are washed with water, dried (Na2SO4) and evaporated in vacuo. Trituration with isopropyl ether provides the desired compound as a brown solid.

Workup

  1. temperatureis heated
  2. temperatureto cool to room temperature
  3. customevaporated to dryness
  4. customThe residue is partitioned between water and EtOAc
  5. extractionthe aqueous phase is extracted (2×) with EtOAc
  6. washThe combined organic phases are washed with water
  7. dry with materialdried (Na2SO4)
  8. customevaporated in vacuo

Sources & evidence

ORD record
ord-764d689ece6847c4980131a94c55eda9
Source dataset
uspto-grants-2012_07
Patent number
US08211902B2

Reaction notes

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