Benzoyl chloride → HCID 18630031, compound

HRID 1440604Notes

Reaction equation

HRID 1440604 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([Si:13]([CH3:16])([CH3:15])[CH3:14])=[C:6]([CH:12]=1)[C:7]([NH:9][CH2:10][CH3:11])=[O:8].C(N(CC)CC)C.[C:24](Cl)(=[O:31])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>C(Cl)Cl.CN(C)C1C=CN=CC=1.O>[C:24]([NH:1][C:2]1[CH:3]=[CH:4][C:5]([Si:13]([CH3:15])([CH3:14])[CH3:16])=[C:6]([CH:12]=1)[C:7]([NH:9][CH2:10][CH3:11])=[O:8])(=[O:31])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

7

Reactant 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 18630262HCID 18630262, compound

Product 1

HCID 18630031HCID 18630031, compound

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of the compound of Example 217 (0.118 g, 0.5 mmol) in CH2Cl2 (10 mL) was added triethylamine (0.14 mL, 1.0 mmol), benzoyl chloride (70 μL, 0.6 mmol) and 4-dimethylaminopyridine (12 mg). The reaction was stirred at RT for 16 h, diluted with water, and extracted with ethyl acetate. The extracts were washed with 0.04N HCl, sat NaHCO3, brine, dried (MgSO4) and concentrated to afford the title compound. The crude product was purified by recrystallization from ethyl acetate/hexanes to afford the title compound as fluffy white crystals (0.129 g, 76%). m.p. 185°-187° C.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extracts were washed with 0.04N HCl
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-bcd2631f5e9a49ba9df708889229c451
Source dataset
uspto-grants-1996_03
Patent number
US05498630

Reaction notes

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