Benzoyl chloride → HCID 18630031, compound

HRID 1458133Notes

Reaction equation

HRID 1458133 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-944c94a556fa470f9604a68400ac7b74
Source dataset
uspto-grants-1998_12
Patent number
US05849723

Reaction notes

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