Water → N-(4-fluorophenyl)-2,2-dimethylpropanamide

HRID 2167191Notes

Reaction equation

HRID 2167191 reaction equation
[F: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>[F: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 8471TriethylamineHCID 97314-FluoroanilineHCID 62493Pivaloyl chloride

Product 1

HCID 310095N-(4-fluorophenyl)-2,2-dimethylpropanamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-fluoroaniline (50.0 g) and triethylamine (157 ml) in CH2Cl2 (700 ml) were added 2,2-dimethyl-propionyl chloride (58.0 ml) over a 30 minutes period. The resulting solution was stirred at r.t. for 2 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 86.0 g of the title compound. M.p. 124-125° C.; Retention Time HPLC 2.57 min; MS (ES+) 196 (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-72c20468247f4d58a65c7421c6adbf9f
Source dataset
uspto-grants-2015_06
Patent number
US09045422B2

Reaction notes

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