Potassium Carbonate → HCID 18354605, compound

HRID 850044Notes

Reaction equation

HRID 850044 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(=O)([O-])[O-].[K+].[K+].[F:17][C:18]1[CH:25]=[CH:24][C:21]([CH2:22]Br)=[CH:20][CH:19]=1>C(#N)C>[F:17][C:18]1[CH:25]=[CH:24][C:21]([CH2:22][O:1][C:2]2[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=2)[C:5]([NH2:7])=[O:6])=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 680214-Fluorobenzyl bromideHCID 3424033-Hydroxybenzamide

Product 1

HCID 18354605HCID 18354605, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To 3-hydroxybenzamide (2.0 mM) under nitrogen was added anhydrous acetonitrile (30 ml), potassium carbonate (2.0 mM), and p-fluorobenzyl bromide (2.0 mM). The mixture was refluxed for 14 hours, and the progress of the reaction monitored by TLC. The excess solvent was removed under vacuum, until dry, and the title compound was recrystallised from hot dichloromethane (minimum amount), and petrol ether 40/60. A white crystalline solid was isolated and dried. Melting point: 161-162° C. Infrared data: KBr disc: cm-1 : 3366; 3171; 1H NMR: d6DMSO: δ=5.23 (s; 2H; CH2); 7.26-7.68 (m; 9H; NH; aromatics); 8.11 (s; 1H; H4);

Workup

  1. temperatureThe mixture was refluxed for 14 hours
  2. customThe excess solvent was removed under vacuum
  3. customuntil dry
  4. customthe title compound was recrystallised from hot dichloromethane (minimum amount), and petrol ether 40/60
  5. customA white crystalline solid was isolated
  6. customdried

Sources & evidence

ORD record
ord-ec57b07b2f3c419c90151509a2db2f9e
Source dataset
uspto-grants-2000_01
Patent number
US06015827

Reaction notes

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