Potassium Carbonate → HCID 28825277, compound

HRID 1406338Notes

Reaction equation

HRID 1406338 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH2:8])=[O:7])=[CH:4][CH:3]=1.F[C:12]1[CH:19]=[CH:18][C:15]([CH:16]=[O:17])=[CH:14][CH:13]=1.C([O-])([O-])=O.[K+].[K+]>CS(C)=O>[CH:16]([C:15]1[CH:18]=[CH:19][C:12]([O:1][C:2]2[CH:10]=[CH:9][C:5]([C:6]([NH2:8])=[O:7])=[CH:4][CH:3]=2)=[CH:13][CH:14]=1)=[O:17]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 650524-HydroxybenzamideHCID 680234-Fluorobenzaldehyde

Product 1

HCID 28825277HCID 28825277, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
140 °C

Procedure

3.1 g (23 mmol) of 4-hydroxybenzamide and 2.8 g (23 mmol) of 4-fluorobenzaldehyde were dissolved in DMSO, combined with 4.4 g (32 mmol) of K2CO3 and stirred overnight at 140° C., filtered through basic Alox, washed with DMF, concentrated by rotary evaporation and purified by chromatography (silica gel column, dichloromethane with a gradient of 10-20% methanol). As there was still some DMF present, the mixture was triturated with water, suction filtered and dried

Workup

  1. filtrationfiltered through basic Alox
  2. washwashed with DMF
  3. concentrationconcentrated by rotary evaporation
  4. custompurified by chromatography (silica gel column, dichloromethane with a gradient of 10-20% methanol)
  5. customthe mixture was triturated with water, suction
  6. filtrationfiltered
  7. customdried

Sources & evidence

ORD record
ord-c437d0d0eb9845598a90d7de0365f531
Source dataset
uspto-grants-2014_12
Patent number
US08916589B2

Reaction notes

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