Chlorotrimethylsilane → HCID 4296438, compound

HRID 2206986Notes

Reaction equation

HRID 2206986 reaction equation
[CH3:1][N:2]([CH3:11])[C:3]1[CH:10]=[CH:9][C:6]([CH:7]=O)=[CH:5][CH:4]=1.[C:12]1([CH2:18][C:19]([NH2:21])=[O:20])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C[Si](Cl)(C)C>ClCCCl>[CH3:1][N:2]([CH3:11])[C:3]1[CH:10]=[CH:9][C:6]([CH:7]([NH:21][C:19](=[O:20])[CH2:18][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[NH:21][C:19](=[O:20])[CH2:18][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 6397ChlorotrimethylsilaneHCID 74794-(Dimethylamino)BenzaldehydeHCID 7680Benzeneacetamide

Product 1

HCID 4296438HCID 4296438, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
70 °C

Procedure

To a suspension of 4-(dimethylamino)benzaldehyde (149 mg, 1 mmol) and 2-phenylacetamide (270 mg, 2 mmol) in 2 mL anhydrous DCE, TMSCl (216 mg, 2 mmol) was added. The mixture was heated at 70° C. for 12 h, then cooled to room temperature and the crude product precipitated from the solution. The crude product was recrystallized with methanol and hexane to give the final product (140 mg, 35%). 1H NMR (400 MHz, DMSO-d6) δ 8.89 (d, J=8.0 Hz, 2H), 7.59 (s, 2H), 7.41 (d, J=8.8 Hz, 2H), 7.21-7.32 (m, 10H), 6.54 (t, J=8.0 Hz, 1H), 3.52 (dd, J=14.0, 15.6 Hz, 4H), 3.06 (s, 6H).

Workup

  1. additionwas added
  2. temperaturecooled to room temperature
  3. customthe crude product precipitated from the solution
  4. customThe crude product was recrystallized with methanol and hexane

Sources & evidence

ORD record
ord-9710aa2d6f914eb7b27d15409a9cf8ca
Source dataset
uspto-grants-2016_06
Patent number
US09376380B2

Reaction notes

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