4-Chloroaniline → HCID 19029387, compound

HRID 2256285Notes

Reaction equation

HRID 2256285 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]2[CH2:15][C:14](=[O:16])[O:13][C:11](=[O:12])[CH2:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8].[Cl:17][C:18]1[CH:24]=[CH:23][C:21]([NH2:22])=[CH:20][CH:19]=1.C(N(CC)CC)C>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]([CH2:10][C:11]([NH:22][C:21]2[CH:23]=[CH:24][C:18]([Cl:17])=[CH:19][CH:20]=2)=[O:12])[CH2:15][C:14]([OH:13])=[O:16])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

5

Reactant 3

HCID 78124-ChloroanilineHCID 8471TriethylamineHCID 543639424-(3,4-Dichlorophenyl)oxane-2,6-dione

Product 1

HCID 19029387HCID 19029387, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

3-(3,4-Dichlorophenyl)glutaric anhydride in CH2Cl2 (75 mL) at 0° C. was treated sequentially with 4-chloroaniline (2.25 g), triethylamine (1.79 g) and N,N-dimethylaminopyridine (trace). The mixture was stirred at 0° C. for two hours then allowed to warm to room temperature and stirred for 12 hours. The reaction mixture was washed with 1N HCl (3×50 mL) and water (50 mL). The organic layers were dried over MgSO4, filtered and concentrated to afford the title compound (4.9 g).

Workup

  1. temperatureto warm to room temperature
  2. stirringstirred for 12 hours
  3. washThe reaction mixture was washed with 1N HCl (3×50 mL) and water (50 mL)
  4. dry with materialThe organic layers were dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-8db4450a51f544a7a379d528dac149da
Source dataset
uspto-grants-1997_08
Patent number
US05654316

Reaction notes

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