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

HRID 2195802Notes

Reaction equation

HRID 2195802 reaction equation
[Cl:1][C:2]1[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=1[NH2:4].[OH-].[Na+].[CH3:11][C:12]([CH3:17])([CH3:16])[C:13](Cl)=[O:14]>CC(OC)(C)C>[Cl:1][C:2]1[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=1[NH:4][C:13](=[O:14])[C:12]([CH3:17])([CH3:16])[CH3:11]

Participants

5

Reactant 3

HCID 72402-ChloroanilineHCID 14798Sodium HydroxideHCID 62493Pivaloyl chloride

Product 1

HCID 143933Propanamide, N-(2-chlorophenyl)-2,2-dimethyl-Yield 97%

Reagents, catalysts & solvents 1

HCID 15413tert-Butyl methyl etherSolvent

Procedure

To a solution of 2-chloroaniline 46 (200 mL, 1.9 mol) in MTBE (950 mL) in an ice-water bath was added 25 wt % NaOH (480 g, 3 mol). Trimethylacetyl chloride (248.5 mL, 2.02 mol) was then added dropwise and the reaction was stirred overnight at rt. The organic layer was separated, washed with brine (1.0 L) and water (1.0 L), dried over sodium sulfate, and concentrated in vacuo to give 47 (390 g, 97%) as a white solid.

Workup

  1. customThe organic layer was separated
  2. washwashed with brine (1.0 L) and water (1.0 L)
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-456d6d8902b64790b7d57017029d6030
Source dataset
uspto-grants-2012_12
Patent number
US08338425B2

Reaction notes

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