Water → HCID 90016075, compound

HRID 591151Notes

Reaction equation

HRID 591151 reaction equation
[CH2:1]([N:5]([CH2:19][CH2:20][CH2:21][CH3:22])[CH2:6][CH2:7][CH2:8][O:9][C:10]1[CH:18]=[CH:17][C:13]([C:14](Cl)=[O:15])=[CH:12][CH:11]=1)[CH2:2][CH2:3][CH3:4].[CH2:23]([NH:25][CH2:26][CH3:27])[CH3:24].C[Si](Cl)(C)C.O>ClCCl>[CH2:1]([N:5]([CH2:19][CH2:20][CH2:21][CH3:22])[CH2:6][CH2:7][CH2:8][O:9][C:10]1[CH:18]=[CH:17][C:13]([C:14]([N:25]([CH2:26][CH3:27])[CH2:23][CH3:24])=[O:15])=[CH:12][CH:11]=1)[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 4

HCID 962WaterHCID 6397ChlorotrimethylsilaneHCID 8021DiethylamineHCID 10109258Benzoyl chloride, 4-[3-(dibutylaMino)propoxy]-

Product 1

HCID 90016075HCID 90016075, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

6.5 g of 4-(3-dibutylaminopropoxyl)benzoyl chloride (V) (0.02 mol) is dissolved in 60 mL of dichloromethane. 1.46 g of diethylamine (0.02 mol, 1 eq) is added and the reaction mixture is cooled to 0° C. 0.43 g TMSCl (0.004 mol, 0.2 eq) is added in 5 min. The reaction mixture is heated to room temperature and stirred for 5 hours. 50 mL of water is added to the mixture, it is stirred for 15 min and the phases are separated. The organic phase is washed with 30 mL of water then it is concentrated. The residue is purified by column chromatography (spheric silica; eluent: toluene:MTBE:methanol=5:4:1) to give 5.58 g of the title compound (VId) (77%) as a yellowish solid.

Workup

  1. temperatureThe reaction mixture is heated to room temperature
  2. stirringis stirred for 15 min
  3. customthe phases are separated
  4. washThe organic phase is washed with 30 mL of water
  5. concentrationit is concentrated
  6. customThe residue is purified by column chromatography (spheric silica; eluent: toluene:MTBE:methanol=5:4:1)

Sources & evidence

ORD record
ord-0e0c4a41fa6c4a7f85ec205159227673
Source dataset
uspto-grants-2016_01
Patent number
US09238636B2

Reaction notes

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