Triethylamine → HCID 12989090, compound

HRID 612421Notes

Reaction equation

HRID 612421 reaction equation
[C@@H:1]12[CH2:9][CH2:8][C:7](=[O:10])[C@@H:6]1[CH2:5][CH2:4][C:3](=[O:11])[NH:2]2.[CH3:12][C:13]1[CH:21]=[CH:20][C:16]([C:17](Cl)=[O:18])=[CH:15][CH:14]=1.C(N(CC)CC)C>ClCCl>[C:13]1([CH3:12])[CH:21]=[CH:20][C:16]([C:17]([N:2]2[C:3](=[O:11])[CH2:4][CH2:5][C@@H:6]3[C@H:1]2[CH2:9][CH2:8][C:7]3=[O:10])=[O:18])=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 134054-Methylbenzoyl ChlorideHCID 54441068HCID 54441068, compound

Product 1

HCID 12989090HCID 12989090, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In 20 ml of dichloromethane were dissolved 0.3 g of Compound 6b obtained in Example 11 and 0.39 g of 4-methylbenzoyl chloride. Thereto was added dropwise 0.38 ml of triethylamine with ice cooling. The mixture was reacted at room temperature for 12 hours. The reaction mixture was washed with 0.1N hydrochloric acid, with 0.1N aqueous solution of NaOH and then with water, and dried over anhydrous sodium sulfate. After dried, the solvent was removed and the residue was recrystallized to obtain 0.35 g of Compound mentioned above (yield: 66%). Table 6 shows analytical data.

Workup

  1. customThe mixture was reacted at room temperature for 12 hours
  2. washThe reaction mixture was washed with 0.1N hydrochloric acid, with 0.1N aqueous solution of NaOH
  3. dry with materialwith water, and dried over anhydrous sodium sulfate
  4. customAfter dried
  5. customthe solvent was removed
  6. customthe residue was recrystallized

Sources & evidence

ORD record
ord-995af75d2da94a8ca85d923fafd692eb
Source dataset
uspto-grants-1999_12
Patent number
US06004975

Reaction notes

Loading…