Triethylamine → HCID 70194467, compound

HRID 2256297Notes

Reaction equation

HRID 2256297 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:25]=[CH:24][C:21](NC)=[CH:20][CH:19]=1.[CH2:26]([N:28](CC)CC)C>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]([CH2:10][C:11]([NH:28][CH2:26][C:21]2[CH:20]=[CH:19][C:18]([Cl:17])=[CH:25][CH:24]=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 8471TriethylamineHCID 702724-Chloro-N-methylbenzenamineHCID 543639424-(3,4-Dichlorophenyl)oxane-2,6-dione

Product 1

HCID 70194467HCID 70194467, compoundYield 96.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

3-(3,4-Dichlorophenyl)glutaric anhydride (10.0 g) in CH2Cl2 (150 mL) at 0° C. was treated sequentially with 4-chloro-N-methylaniline (6.8 g), triethylamine (4.87 g) and N,N-dimethylaminopyridine (0.5 g). 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 (3×100 mL) and water (100 mL). The organic layers were dried over MgSO4, filtered and concentrated to afford the title compound (14.9 g).

Workup

  1. temperatureto warm to room temperature
  2. stirringstirred for 12 hours
  3. washThe reaction mixture was washed with 1N HCl (3×100 mL) and water (100 mL)
  4. dry with materialThe organic layers were dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-f0b7236f04914c0aafeccfedb4cbefb1
Source dataset
uspto-grants-1997_08
Patent number
US05654316

Reaction notes

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