4-Chloroaniline → HCID 178451334, compound

HRID 603923Notes

Reaction equation

HRID 603923 reaction equation
[CH:1]([C:3]1[CH:17]=[CH:16][C:6]([O:7][CH2:8][C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])=[CH:5][CH:4]=1)=O.[Cl:18][C:19]1[CH:25]=[CH:24][C:22]([NH2:23])=[CH:21][CH:20]=1>C1(C)C=CC=CC=1>[Cl:18][C:19]1[CH:25]=[CH:24][C:22](/[N:23]=[CH:1]/[C:3]2[CH:17]=[CH:16][C:6]([O:7][CH2:8][C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])=[CH:5][CH:4]=2)=[CH:21][CH:20]=1

Participants

4

Reactant 2

HCID 78124-ChloroanilineHCID 639902Tert-butyl 2-(4-formylphenoxy)acetate

Product 1

HCID 178451334HCID 178451334, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

tert-Butyl (4-formylphenoxy)acetate (17.4 g, 73.4 mmol) was dissolved in dry toluene (120 mL) and 4-chloroaniline (9.37 g, 73.4 mmol) was added. The mixture was refluxed in a Dean-Stark apparatus for 20 hours, cooled and concentrated under reduced pressure. Hexane was added and a precipitate formed. This precipitate was filtered, washed twice with cold hexane and dried. This afforded the title compound.

Workup

  1. temperatureThe mixture was refluxed in a Dean-Stark apparatus for 20 hours
  2. temperaturecooled
  3. concentrationconcentrated under reduced pressure
  4. additionHexane was added
  5. customa precipitate formed
  6. filtrationThis precipitate was filtered
  7. washwashed twice with cold hexane
  8. customdried

Sources & evidence

ORD record
ord-5e5f44a9d724402a94fe448885cb0c7b
Source dataset
uspto-grants-2011_03
Patent number
US07906502B2

Reaction notes

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