O-Toluidine → 2,2,2'-Trimethylpropionanilide

HRID 1403962Notes

Reaction equation

HRID 1403962 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][C:7]=1[NH2:8].CCN(CC)CC.[CH3:16][C:17]([CH3:22])([CH3:21])[C:18](Cl)=[O:19]>C(Cl)Cl>[C:2]1([CH3:1])[CH:3]=[CH:4][CH:5]=[CH:6][C:7]=1[NH:8][C:18](=[O:19])[C:17]([CH3:22])([CH3:21])[CH3:16]

Participants

5

Reactant 3

HCID 7242O-ToluidineHCID 8471TriethylamineHCID 62493Pivaloyl chloride

Product 1

HCID 27340052,2,2'-TrimethylpropionanilideYield 91.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of o-tolylamine (21 g, 0.20 mol) and Et3N (22 g, 0.22 mol) in CH2Cl2 was added 2,2-dimethyl-propionyl chloride (25 g, 0.21 mol) at 10° C. After addition, the mixture was stirred overnight at room temperature. The mixture was washed with aq. HCl (5%, 80 mL), saturated aq. NaHCO3 and brine. The organic layer was dried over Na2SO4 and concentrated under vacuum to give N-o-tolylpivalamide (35 g, 91%). 1H NMR (300 MHz, CDCl3) δ 7.88 (d, J=7.2 Hz, 1H), 7.15-7.25 (m, 2H), 7.05 (t, J=7.2 Hz, 1H), 2.26 (s, 3H), 1.34 (s, 9H).

Workup

  1. additionAfter addition
  2. washThe mixture was washed with aq. HCl (5%, 80 mL), saturated aq. NaHCO3 and brine
  3. dry with materialThe organic layer was dried over Na2SO4
  4. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-ed365e3019a44326a7e90801553f7d91
Source dataset
uspto-grants-2014_12
Patent number
US08912199B2

Reaction notes

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