Triethylamine → HCID 70195521, compound

HRID 2256292Notes

Reaction equation

HRID 2256292 reaction equation
[C:1]1([CH:7]2[CH2:13][C:12](=[O:14])[O:11][C:9](=[O:10])[CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cl:15][C:16]1[CH:23]=[CH:22][C:19](NC)=[CH:18][CH:17]=1.[CH2:24]([N:26](CC)CC)C>C(Cl)Cl>[Cl:15][C:16]1[CH:17]=[CH:18][C:19]([CH2:24][NH:26][C:12](=[O:14])[CH2:13][CH:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH2:8][C:9]([OH:11])=[O:10])=[CH:22][CH:23]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 702724-Chloro-N-methylbenzenamineHCID 2978824-Phenyloxane-2,6-dione

Product 1

HCID 70195521HCID 70195521, compoundYield 77.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

3-Phenylglutaric anhydride (2.0 g) in CH2Cl2 (25 mL) at 0° C. was treated sequentially with 4-chloro-N-methylaniline (1.86 g), triethylamine (1.33 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 (2×50 mL) and water (100 mL). The organic layers were dried over MgSO4, filtered and concentrated to afford the title compound (2.7 g).

Workup

  1. temperatureto warm to room temperature
  2. stirringstirred for 12 hours
  3. washThe reaction mixture was washed with 1N HCl (2×50 mL) and water (100 mL)
  4. dry with materialThe organic layers were dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-e9867988fdc1415199ff2fa060905d9a
Source dataset
uspto-grants-1997_08
Patent number
US05654316

Reaction notes

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