Hydrochloric Acid → Propanamide, N-(4-chlorophenyl)-2,2-dimethyl-

HRID 1509880Notes

Reaction equation

HRID 1509880 reaction equation
[Cl:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=1.[C:9](Cl)(=[O:14])[C:10]([CH3:13])([CH3:12])[CH3:11].Cl>N1C=CC=CC=1>[Cl:1][C:2]1[CH:8]=[CH:7][C:5]([NH:6][C:9](=[O:14])[C:10]([CH3:13])([CH3:12])[CH3:11])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 78124-ChloroanilineHCID 62493Pivaloyl chloride

Product 1

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

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 4-chloroaniline (5.0 g, 39.2 mmol) in 25 mL pyridine was added 5.3 mL (43.1 mmol) of pivaloyl chloride and the reaction mixture stirred overnight at room temperature. The mixture was poured into vigorously stirring 6M HCl, and the solids were collected by vacuum filtration, washed well with H2O, and dried in vacuo to yield the title compound. 1H NMR (CDCl3) δ 7.47 (d, J=9.2 Hz, 2H) 7.30 (s, 1H) 7.27 (d, J=8.8 Hz, 2H) 1.32 (s, 9H) MS (ES) m/z=212.1

Workup

  1. additionThe mixture was poured
  2. filtrationthe solids were collected by vacuum filtration
  3. washwashed well with H2O
  4. customdried in vacuo

Sources & evidence

ORD record
ord-a28d770cf52e40a4bd2738b8c36faa8c
Source dataset
uspto-grants-2012_07
Patent number
US08211896B2

Reaction notes

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