4-Chloroaniline → Propanamide, N-(4-chlorophenyl)-2,2-dimethyl-

HRID 440257Notes

Reaction equation

HRID 440257 reaction equation
[Cl:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=1.C([O-])([O-])=O.[Na+].[Na+].[CH3:15][C:16]([CH3:21])([CH3:20])[C:17](Cl)=[O:18]>C(Cl)(Cl)Cl>[Cl:1][C:2]1[CH:8]=[CH:7][C:5]([NH:6][C:17](=[O:18])[C:16]([CH3:21])([CH3:20])[CH3:15])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 78124-ChloroanilineHCID 10340Sodium CarbonateHCID 62493Pivaloyl chloride

Product 1

HCID 182511Propanamide, N-(4-chlorophenyl)-2,2-dimethyl-Yield 87.7%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a 5L 3 necked round bottomed flask with an overhead stirrer was added 4-chloroaniline (127.57 g, 1 mole), 1200 mL of CHCl3, and 1200 mL of saturated aqueous Na2CO3 solution. An addition funnel was attached to the flask and charged with 2,2-dimethylpropanoyl chloride (129 mL, 1.05 mole). The acid chloride was added dropwise to the vigorously stirred mixture over 1 h. The resulting mixture was stirred at ambient temperature for an additional 23 h. Some of the product separated from the mixture as white crystals. These crystals were collected by filtration. The filtrate was transferred to a separatory funnel and the layers were separated. The chloroform layer was washed with water and brine. Drying (MgSO4), filtration, and removal of the solvent in vacuo gave additional product. The two portions of product were combined and recrystallized from boiling EtOAc-hexanes to give 185.6 g of N-(4-chlorophenyl)-2,2-dimethyl propanamide as a white crystalline solid.

Workup

  1. customAn addition funnel was attached to the flask
  2. customSome of the product separated from the mixture as white crystals
  3. filtrationThese crystals were collected by filtration
  4. customThe filtrate was transferred to a separatory funnel
  5. customthe layers were separated
  6. washThe chloroform layer was washed with water and brine
  7. customDrying
  8. filtration(MgSO4), filtration, and removal of the solvent in vacuo
  9. customgave additional product
  10. customrecrystallized

Sources & evidence

ORD record
ord-0b769bee599c4b1ea62a884a5763bd82
Source dataset
uspto-grants-1996_05
Patent number
US05519021

Reaction notes

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