Potassium Carbonate → HCID 19605757, compound

HRID 1603543Notes

Reaction equation

HRID 1603543 reaction equation
[CH:1]([NH:3][C:4]1[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][C:5]=1[C:6]([NH2:8])=[O:7])=[O:2].C(=O)([O-])[O-].[K+].[K+].[CH3:20][O:21][C:22]1[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][C:23]=1[CH2:24]Br>CN(C)C=O>[CH3:20][O:21][C:22]1[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][C:23]=1[CH2:24][O:13][C:10]1[CH:11]=[CH:12][C:4]([NH:3][CH:1]=[O:2])=[C:5]([CH:9]=1)[C:6]([NH2:8])=[O:7]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 5920212-(Bromomethyl)-1,4-dimethoxybenzeneHCID 19605779HCID 19605779, compound

Product 1

HCID 19605757HCID 19605757, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 140 mg of 2-formylamino-5-hydroxybenzamide in 15 ml of dry dimethylformamide is treated subsequently with 160 mg of potassium carbonate and 180 mg of 2,5-dimethoxybenzylbromide. The mixture is stirred at room temperature for 4 hours, and then the solvent is distilled off in vacuo. The residue is partitioned between water and ethyl acetate, and the separated organic layer is dried over magnesium sulfate and evaporated in vacuo. Purification of the crude product thus obtained by silica gel chromatography (ethyl acetate) gives the title compound as colourless crystals. mp: 135-138°.

Workup

  1. distillationthe solvent is distilled off in vacuo
  2. customThe residue is partitioned between water and ethyl acetate
  3. dry with materialthe separated organic layer is dried over magnesium sulfate
  4. customevaporated in vacuo
  5. customPurification of the crude product
  6. customthus obtained by silica gel chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-8f5f39c846a54056a5963a992cae2291
Source dataset
uspto-grants-1999_11
Patent number
US05990116

Reaction notes

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