Potassium Carbonate → HCID 18354619, compound

HRID 850043Notes

Reaction equation

HRID 850043 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+].[Br:17][C:18]1[CH:25]=[CH:24][C:21]([CH2:22]Br)=[CH:20][CH:19]=1>C(#N)C>[Br: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 685274-Bromobenzyl bromideHCID 3424033-Hydroxybenzamide

Product 1

HCID 18354619HCID 18354619, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To 3-hydroxybenzamide (2.0 mM) under nitrogen was added anhydrous acetonitrile (20 ml), potassium carbonate (2.0 mM), and p-bromobenzyl bromide (2.0 mM). The mixture was refluxed for 3 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). A white crystalline solid was isolated and dried. Melting point: 160-161° C.; Infrared data: cm-1 : KBr disc: 3323; 3146; 1670; 1622. 1H NMR: d6DMSO: δ=5.26 (s; 2H; CH2); 7.3 (dd; 1H: H4); 7.49-7.75 (m, 9H; PhBr; NH2 ; PhO); 13C NMR: d6DMSO: δ=114.031; 118.123; 120.402; 121.295; 129.704; 130.107; 131.690; 136.094; 136.723; 158.371; 167.843. Mass spectra: m/z: EI: 307 (M+1); 262; 212; 169 (100%) 101;90. Elemental analysis: Expect C: 55.26%; H: 3.29%; N: 4.61%; Found C: 54.61%; H: 3.66%; N: 4.47%.

Workup

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

Sources & evidence

ORD record
ord-45b6a1d1dbe04ccb8e3be1f298be13d9
Source dataset
uspto-grants-2000_01
Patent number
US06015827

Reaction notes

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