Potassium Carbonate → HCID 353402, compound

HRID 1586613Notes

Reaction equation

HRID 1586613 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([NH2:7])=[O:6].[C:11]([O:14][CH2:15][CH2:16]Br)(=[O:13])[CH3:12].C([O-])([O-])=O.[K+].[K+]>CN(C)C=O>[C:11]([O:14][CH2:15][CH2:16][O:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([NH2:7])=[O:6])(=[O:13])[CH3:12]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 135641-Acetoxy-2-bromoethaneHCID 3424033-Hydroxybenzamide

Product 1

HCID 353402HCID 353402, compoundYield 65.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
25 °C

Procedure

A mixture of 3-hydroxybenzamide (3.0 g, 21.9 mmol) prepared as in Example 1, 2-bromoethyl acetate (11.9 g, 70.9 mmol), and K2CO3 (5.7 g, 41.2 mmol) in 40 cc dry dimethyl formamide (DMF) was stirred at 25° C. for 48 hours and filtered. The filtrate was evaporated in vacuo and the resulting residue was recrystallized from 90% EtOH(H2O) to give 3.2 g (65%) of the desired product as a white crystalline powder, mp 121°-122° C. Here, as in the other examples, the product compound was identified by elemental analysis as well as by IR and mass spectroscopy methods.

Workup

  1. filtrationfiltered
  2. customThe filtrate was evaporated in vacuo
  3. customthe resulting residue was recrystallized from 90% EtOH(H2O)

Sources & evidence

ORD record
ord-14518b6c025543b6aaf533c1a12d278b
Source dataset
uspto-grants-1993_06
Patent number
US05215738

Reaction notes

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