Ammonium Hydroxide → HCID 18963775, compound

HRID 2226886Notes

Reaction equation

HRID 2226886 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[O:10][C:9]([C:11](O)=[O:12])=[C:8]([O:14][CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[C:7]=2[CH:22]=1.C(N1C=CN=C1)([N:25]1C=CN=C1)=O.[OH-].[NH4+]>O1CCCC1.C(OCC)(=O)C>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[O:10][C:9]([C:11]([NH2:25])=[O:12])=[C:8]([O:14][CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[C:7]=2[CH:22]=1

Participants

6

Reactant 3

HCID 14923Ammonium HydroxideHCID 682631,1'-CarbonyldiimidazoleHCID 13961722HCID 13961722, compound

Product 1

HCID 18963775HCID 18963775, compoundYield 47%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A suspension of 5-methoxy-3-(phenylmethoxy)-2-benzofurancarboxylic acid (157 mg, 0.50 mmol) and 1,1'-carbonyldiimidazole (96 mg, 0.59 mmol) in 15 mL of tetrahydrofuran is heated at reflux for 1.5 hours. The reaction solution is cooled to room temperature, aqueous ammonium hydroxide (1 mL) is added and the reaction mixture is stirred at room temperature for 1 hour. The reaction is diluted with ethyl acetate and washed with brine. The organic phase is dried over magnesium sulfate, filtered, and concentrated in vacuo. Chromatography eluting with ethyl acetate:hexane (1:1) provides 5-methoxy-3-(phenylmethoxy)-2-benzofurancarboxamide in 47% yield; mp=70°-72° C.

Workup

  1. temperatureis heated
  2. temperatureat reflux for 1.5 hours
  3. washwashed with brine
  4. dry with materialThe organic phase is dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. washChromatography eluting with ethyl acetate:hexane (1:1)

Sources & evidence

ORD record
ord-103e4d44f5c74757a6ad292921d5e554
Source dataset
uspto-grants-1994_09
Patent number
US05350748

Reaction notes

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