4-Chloroaniline → HCID 3092418, compound

HRID 554711Notes

Reaction equation

HRID 554711 reaction equation
[Br:1][C:2]1[CH:16]=[CH:15][C:5]([C:6]([NH:8][CH:9](O)[C:10]([Cl:13])([Cl:12])[Cl:11])=[O:7])=[CH:4][CH:3]=1.P(Cl)(Cl)(Cl)(Cl)Cl.BrC1C=CC(C(NC(Cl)C(Cl)(Cl)Cl)=O)=CC=1.[Cl:39][C:40]1[CH:46]=[CH:45][C:43]([NH2:44])=[CH:42][CH:41]=1>C(Cl)(Cl)Cl>[Br:1][C:2]1[CH:16]=[CH:15][C:5]([C:6]([NH:8][CH:9]([NH:44][C:43]2[CH:45]=[CH:46][C:40]([Cl:39])=[CH:41][CH:42]=2)[C:10]([Cl:13])([Cl:12])[Cl:11])=[O:7])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 78124-ChloroanilineHCID 24819Phosphorus pentachlorideHCID 3090003HCID 3090003, compoundHCID 591926354-Bromo-N-(1,2,2,2-tetrachloroethyl)benzamide

Product 1

HCID 3092418HCID 3092418, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
50 °C

Procedure

A solution of 4-bromo-N-(2,2,2-trichloro-1-hydroxyethyl)benzamide (0.67 g, 1.93 mmol) in chloroform (15 mL) was treated with PCl5 (0.42 g, 1.91 mmol). The mixture was heated to 50° C. for 30 minutes before cooling to room temperature and pouring into crushed ice. The organic layer was dried over MgSO4 and filtered. The solution of 4-bromo-N-(1,2,2,2-tetrachloroethyl)benzamide was cooled to room temperature before addition of 4-chloroaniline (0.52 mL, 4.0 mmol), and the mixture was allowed to stir for 18 hours. The mixture was quenched with 2 M HCl and extracted with ether. The organic solution was dried over MgSO4, filtered, and concentrated onto silica gel. The material was purified on an MPLC with 7:3 CH2Cl2:hexanes to give 4-bromo-N-(2,2,2-trichloro-1-(4-chlorophenylamino)ethyl)benzamide (Compound 6) as a solid. The product may be further purified by an appropriate recrystallization such as in ether.

Workup

  1. temperaturebefore cooling to room temperature
  2. additionpouring
  3. custominto crushed ice
  4. dry with materialThe organic layer was dried over MgSO4
  5. filtrationfiltered
  6. customThe mixture was quenched with 2 M HCl
  7. extractionextracted with ether
  8. dry with materialThe organic solution was dried over MgSO4
  9. filtrationfiltered
  10. concentrationconcentrated onto silica gel
  11. customThe material was purified on an MPLC with 7:3 CH2Cl2

Sources & evidence

ORD record
ord-53b914c76ffd408b92c4bd9d22d53f92
Source dataset
uspto-grants-2011_11
Patent number
US08049037B2

Reaction notes

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