Benzoyl chloride → HCID 18630031, compound

HRID 356413Notes

Reaction equation

HRID 356413 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-25731b82606f4dc6b544d2d531bbc099
Source dataset
uspto-grants-1998_11
Patent number
US05834447

Reaction notes

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