Aniline → HCID 90016577, compound

HRID 591152Notes

Reaction equation

HRID 591152 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].[NH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.C(=O)([O-])[O-].[K+].[K+]>CCCCCC>[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]([NH:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[O:15])=[CH:12][CH:11]=1)[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 6115AnilineHCID 11430Potassium CarbonateHCID 10109258Benzoyl chloride, 4-[3-(dibutylaMino)propoxy]-

Product 1

HCID 90016577HCID 90016577, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Conditions

Temperature
50 °C

Procedure

6.5 g of 4-(3-dibutylaminopropoxyl)benzoyl chloride (V) (0.02 mol) is dissolved in 60 mL of n-hexane. 1.86 g of aniline (0.02 mol, 1 eq) and 2.76 g of potassium carbonate (0.02 mol, 1 eq) are added. The reaction mixture is heated to 50° C. and stirred for 4 hours. After the reaction the solid inorganic salt is filtered, washed with 2×10 mL of n-hexane and the filtrate is concentrated. The residue is purified by column chromatography (spheric silica; eluent: toluene:MTBE:methanol=5:4:1) to give 6.50 g of the title compound (VIe) (85%) as a yellow solid.

Workup

  1. customAfter the reaction the solid inorganic salt
  2. filtrationis filtered
  3. washwashed with 2×10 mL of n-hexane
  4. concentrationthe filtrate is concentrated
  5. customThe residue is purified by column chromatography (spheric silica; eluent: toluene:MTBE:methanol=5:4:1)

Sources & evidence

ORD record
ord-64f4bcbbc2944f88a6dffba8a1ec04e1
Source dataset
uspto-grants-2016_01
Patent number
US09238636B2

Reaction notes

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