4-Iodobenzoyl chloride → HCID 25127626, compound

HRID 1253390Notes

Reaction equation

HRID 1253390 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][Si:5]([O:10][CH3:11])([O:8][CH3:9])[O:6][CH3:7].[I:12][C:13]1[CH:21]=[CH:20][C:16]([C:17](Cl)=[O:18])=[CH:15][CH:14]=1>ClCCl>[I:12][C:13]1[CH:21]=[CH:20][C:16]([C:17]([NH:1][CH2:2][CH2:3][CH2:4][Si:5]([O:10][CH3:11])([O:6][CH3:7])[O:8][CH3:9])=[O:18])=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 743734-Iodobenzoyl chlorideHCID 83756Aminopropyltrimethoxysilane

Product 1

HCID 25127626HCID 25127626, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

4-Iodo-N-[3-(trimethoxysilyl)propyl]-benzamide (1) was prepared, as illustrated in FIG. 5, where a solution of 3-aminopropyltrimethoxysilane (1.78 mL, 10 mmol) in 10 mL of dichloromethane was added dropwise to a suspension of 4-iodobenzoyl chloride (1.33 g, 5 mmol) in 20 mL of dichloromethane at 0° C. The mixture was stirred for 1 hour and solvent was evaporated in vacuo. The residue was purified by column chromatography on silica using 2% methanol in chloroform. The solvent was removed by rotary evaporation to give a viscous oil. 1H NMR (300 MHz, CDCl3): δ 0.70 (t, J=8.1 Hz, 2H), 1.73 (m, 2H), 3.42 (m, 2H), 6.64 (br, 1H), 7.49 (d, J=8.7 Hz, 2H), 7.76 (d, J=8.7 Hz, 2H). 13C NMR (75 MHz, CDCl3): δ 6.81, 22.78, 42.54, 50.89, 98.41, 128.78, 134.44, 137.91, 167.03. HRMS calculated for C13H20INO4Si 409.0206, found 410.0295 (MH+).

Workup

  1. customsolvent was evaporated in vacuo
  2. customThe residue was purified by column chromatography on silica using 2% methanol in chloroform
  3. customThe solvent was removed by rotary evaporation
  4. customto give a viscous oil

Sources & evidence

ORD record
ord-bd5bc1dda0664f6697e9d4323fc3e08c
Source dataset
uspto-grants-2013_06
Patent number
US08455265B2

Reaction notes

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