Triethylamine → HCID 19029352, compound

HRID 2256329Notes

Reaction equation

HRID 2256329 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].[CH3:17][NH:18][CH2:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.C(N(CC)CC)C>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]([CH2:10][C:11]([N:18]([CH2:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH3:17])=[O:12])[CH2:15][C:14]([OH:13])=[O:16])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 11503N-MethylbenzeneethanamineHCID 543639424-(3,4-Dichlorophenyl)oxane-2,6-dione

Product 1

HCID 19029352HCID 19029352, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

3-(3,4-Dichlorophenyl)glutaric anhydride (3.4 g) in CH2Cl2 (50 mL) at 0° C. was treated sequentially with N-methylphenethylamine (2.4 mL), triethylamine (2.3 mL) and N,N-dimethylaminopyridine (162 mg). The mixture was stirred at 0° C. for two hours then allowed to warm to room temperature and stirred for 20 hours. The reaction mixture was washed with 1N HCl (1×100 mL) and brine (1×100 mL). The organic layers were dried over MgSO4, filtered and concentrated to afford the title compound (4.6 g).

Workup

  1. temperatureto warm to room temperature
  2. stirringstirred for 20 hours
  3. washThe reaction mixture was washed with 1N HCl (1×100 mL) and brine (1×100 mL)
  4. dry with materialThe organic layers were dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-c18d68c3d2c345df9eaf92c998f99cb3
Source dataset
uspto-grants-1997_08
Patent number
US05654316

Reaction notes

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