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

HRID 1092751Notes

Reaction equation

HRID 1092751 reaction equation
[Cl:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH3:16][C:17]([CH3:22])([CH3:21])[C:18](Cl)=[O:19].O>C(Cl)(Cl)Cl>[Cl:1][C:2]1[CH:8]=[CH:7][C:5]([NH:6][C:18](=[O:19])[C:17]([CH3:22])([CH3:21])[CH3:16])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 78124-ChloroanilineHCID 8471TriethylamineHCID 62493Pivaloyl chloride

Product 1

HCID 182511Propanamide, N-(4-chlorophenyl)-2,2-dimethyl-Yield 84.6%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 4-chloroaniline (25.51 g) and triethylamine (69.73 ml) in chloroform (350 ml) were added 2,2-dimethyl-propionyl chloride (25.32 g) over a 30 minutes period. The resulting solution was stirred at r.t. for 1 hour, then water was added and the mixture extracted three times with ethyl acetate. The combined organic layers were dried over sodium sulfate and concentrated in vacuo to afford 35.8 g of product. M.p. 149-150° C.; Retention Time HPLC 2.83 min; MS (ES+) 212 (M+H+).

Workup

  1. extractionthe mixture extracted three times with ethyl acetate
  2. dry with materialThe combined organic layers were dried over sodium sulfate
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-450e504f740347e3aa82fe4df5dd3985
Source dataset
uspto-grants-2012_03
Patent number
US08129534B2

Reaction notes

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