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

HRID 239814Notes

Reaction equation

HRID 239814 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-6942fe117fe941d38e5134b3ec30d6d7
Source dataset
uspto-grants-2014_02
Patent number
US08642808B2

Reaction notes

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