Diphenylamine → 3-chloro-N,N-diphenylpropanamide

HRID 345459Notes

Reaction equation

HRID 345459 reaction equation
[C:1]1([NH:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cl:14][CH2:15][CH2:16][C:17](Cl)=[O:18]>O1CCCC1>[Cl:14][CH2:15][CH2:16][C:17]([N:7]([C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)=[O:18]

Participants

4

Reactant 2

HCID 11487DiphenylamineHCID 693643-Chloropropionyl chloride

Product 1

HCID 33314083-chloro-N,N-diphenylpropanamideYield 48.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 40.6 g (0.240 mole) of diphenylamine in 150 ml of tetrahydrofuran (THF) was added dropwise a solution of 20.0 g (0.160 mole) of 3-chloropropionyl chloride in 100 ml of THF. The reaction mixture was stirred mechanically and the temperature maintained between 5° and 15° C. throughout the addition. After the final addition, the solution was filtered to remove solid precipitates, and the filtrate was concentrated under reduced pressure. The residue was partitioned between methylene chloride and water (200 ml each). The methylene chloride layer was washed with water and brine, dried (MgSO4) and concentrated under reduced pressure to give an amorphous solid. The solid was recrystallized from THF to yield 20.0 g (48%) of the title compound as a white, crystalline solid, mp 93°-94° C.

Workup

  1. temperaturethe temperature maintained between 5° and 15° C. throughout the addition
  2. additionAfter the final addition
  3. filtrationthe solution was filtered
  4. customto remove solid
  5. customprecipitates
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. customThe residue was partitioned between methylene chloride and water (200 ml each)
  8. washThe methylene chloride layer was washed with water and brine
  9. dry with materialdried (MgSO4)
  10. concentrationconcentrated under reduced pressure
  11. customto give an amorphous solid
  12. customThe solid was recrystallized from THF

Sources & evidence

ORD record
ord-9b074839ea5c4e9099d894bf23299e26
Source dataset
uspto-grants-1991_10
Patent number
US05057524

Reaction notes

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