Potassium Carbonate → HCID 90016629, compound

HRID 591148Notes

Reaction equation

HRID 591148 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].[OH-].[NH4+:24].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]([NH2:24])=[O:15])=[CH:12][CH:11]=1)[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 14923Ammonium HydroxideHCID 10109258Benzoyl chloride, 4-[3-(dibutylaMino)propoxy]-

Product 1

HCID 90016629HCID 90016629, compoundYield 87.1%

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. 2.50 g of ammonium hydroxide (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 3 hours. After the reaction the solid inorganic salt is filtered, washed with 2×5 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 5.34 g of the title compound (VIa) (87%) as a yellowish solid.

Workup

  1. customAfter the reaction the solid inorganic salt
  2. filtrationis filtered
  3. washwashed with 2×5 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-8380f829d0d7496abf48572db6a89072
Source dataset
uspto-grants-2016_01
Patent number
US09238636B2

Reaction notes

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