Potassium Carbonate → HCID 19878308, compound

HRID 1885913Notes

Reaction equation

HRID 1885913 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[C:20]3[C:15](=[CH:16][CH:17]=[C:18]4[CH:24]=[CH:23][CH:22]=[CH:21][C:19]4=3)[C:14]3[C:9]2=[CH:10][C:11]([O:25][CH3:26])=[CH:12][CH:13]=3)=[CH:4][CH:3]=1.Cl.Cl[CH2:29][CH2:30][N:31]([CH:35]([CH3:37])[CH3:36])[CH:32]([CH3:34])[CH3:33].C(=O)([O-])[O-].[K+].[K+]>C(C(C)=O)C>[CH3:26][O:25][C:11]1[CH:10]=[C:9]2[C:14]([C:15]3[C:20]([CH:8]2[C:5]2[CH:4]=[CH:3][C:2]([O:1][CH2:29][CH2:30][N:31]([CH:35]([CH3:37])[CH3:36])[CH:32]([CH3:34])[CH3:33])=[CH:7][CH:6]=2)=[C:19]2[CH:21]=[CH:22][CH:23]=[CH:24][C:18]2=[CH:17][CH:16]=3)=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 779422-Chloroethyldiisopropylammonium chlorideHCID 19878336HCID 19878336, compound

Product 1

HCID 19878308HCID 19878308, compound

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A 7 g portion of the compound of Example 1 was reacted with 6.6 g of 2-chloroethyl-bis(isopropyl)amine hydrochloride in the presence of 12.2 g of potassium carbonate in 75 ml of methyl ethyl ketone. The mixture was stirred under reflux for 72 hours, and was then worked up as described in Example 5. The impure product was chromatographed over silica gel with a gradient solvent proceeding from toluene to 9:1 toluene:ethyl acetate. Concentration of the product-containing fractions gave 4.16 g of the desired product, m.p. 106°-115° C.

Workup

  1. temperatureunder reflux for 72 hours
  2. customThe impure product was chromatographed over silica gel with a gradient solvent

Sources & evidence

ORD record
ord-718800ab934c4c7ab4d6adcd86044a14
Source dataset
uspto-grants-1992_09
Patent number
US05147880

Reaction notes

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