N-Methylaniline → 3-chloro-N-methyl-N-phenylpropanamide

HRID 345460Notes

Reaction equation

HRID 345460 reaction equation
[CH3:1][NH:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[Cl:9][CH2:10][CH2:11][C:12](Cl)=[O:13]>O1CCCC1>[Cl:9][CH2:10][CH2:11][C:12]([N:2]([CH3:1])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1)=[O:13]

Participants

4

Reactant 2

HCID 7515N-MethylanilineHCID 693643-Chloropropionyl chloride

Product 1

HCID 33143863-chloro-N-methyl-N-phenylpropanamideYield 92.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 107.2 g (1.00 mole) of N-methylaniline in 150 ml of tetrahydrofuran was added dropwise to a solution of 90.4 g (0.71 mole) of 3-chloropropionyl chloride in 250 ml of tetrahydrofuran. The reaction temperature was maintained between 5° and 15° C. throughout the addition. After the final addition, the solution was filtered to remove a solid precipitate, and the filtrate was concentrated under reduced pressure to yield 130.0 g (91%) of a dark oil. An analytical sample was prepared by filtering the oil through a small bed of silica gel and eluting with ethyl acetate-hexane (1:5). The fractions containing the desired product were combined and concentrated under reduced pressure to give a light-yellow liquid. The liquid was partitioned between ethyl acetate and a saturated sodium bicarbonate solution. The ethyl acetate layer was washed with water and brine, dried (MgSO4), and concentrated under reduced pressure to give the title compound as a light-yellow oil.

Workup

  1. temperatureThe reaction temperature was maintained between 5° and 15° C. throughout the addition
  2. additionAfter the final addition
  3. filtrationthe solution was filtered
  4. customto remove a solid precipitate
  5. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-732720d4319d499c9cb96c67afdef9dc
Source dataset
uspto-grants-1991_10
Patent number
US05057524

Reaction notes

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