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

HRID 377952Notes

Reaction equation

HRID 377952 reaction equation
[Cl:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=1.[OH-].[Na+].O.[CH3:12][C:13]([CH3:18])([CH3:17])[C:14](Cl)=[O:15]>COC(C)(C)C>[Cl:1][C:2]1[CH:8]=[CH:7][C:5]([NH:6][C:14](=[O:15])[C:13]([CH3:18])([CH3:17])[CH3:12])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 78124-ChloroanilineHCID 14798Sodium HydroxideHCID 62493Pivaloyl chloride

Product 1

HCID 182511Propanamide, N-(4-chlorophenyl)-2,2-dimethyl-Yield 97.2%

Reagents, catalysts & solvents 1

HCID 15413tert-Butyl methyl etherSolvent

Conditions

Temperature
15 °C

Procedure

4-Chloroaniline (52.7 kg, 413 mol) was dissolved in a mixture of t-butyl methyl ether (180 kg), 30% aqueous sodium hydroxide (61.6 kg, 463 mol) and water (24.2 kg), then cooled to 15° C. To the resulting slurry was charged trimethylacetyl chloride (52.2 kg, 448 mol) over 1 h, keeping the temperature below 40° C. After stirring 30 min at 30° C. the slurry was cooled to -10° C. and held for 2 hours. The product was collected by filtration, washed with a solution of 90/10 water/methanol (175 kg), then dried in vacuo to give 85 kg (97% yield) of the title compound as a crystalline solid: mp 152-153° C.; 1H NMR (300 MHz, CDCl3) δ7.48 (d, J=9 Hz, 2H) 7.28 (d, J=9 Hz, 2H); 13C NMR (75 MHz, CDCl3) d 176.7, 136.6, 129.1, 128.9, 121.4, 39.6, 27.6.

Workup

  1. customthe temperature below 40° C
  2. temperaturewas cooled to -10° C.
  3. waitheld for 2 hours
  4. filtrationThe product was collected by filtration
  5. washwashed with a solution of 90/10 water/methanol (175 kg)
  6. customdried in vacuo

Sources & evidence

ORD record
ord-fa9d21d31b994eeeb8730e43be2fbef8
Source dataset
uspto-grants-2000_02
Patent number
US06028237

Reaction notes

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