Ammonium Hydroxide → HCID 10846515, compound

HRID 2226879Notes

Reaction equation

HRID 2226879 reaction equation
[CH3:1][CH:2]([O:4][C:5]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[O:7][C:6]=1[C:14]([OH:16])=O)[CH3:3].C(N1C=CN=C1)([N:19]1C=CN=C1)=O.[OH-].[NH4+]>O1CCCC1.C(OCC)(=O)C>[CH3:1][CH:2]([O:4][C:5]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[O:7][C:6]=1[C:14]([NH2:19])=[O:16])[CH3:3]

Participants

6

Reactant 3

HCID 14923Ammonium HydroxideHCID 682631,1'-CarbonyldiimidazoleHCID 10704137HCID 10704137, compound

Product 1

HCID 10846515HCID 10846515, compoundYield 77%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A suspension of 3-(1-methylethoxy)-2-benzofurancarboxylic acid (200 mg, 0.91 mmol) and 1,1'-carbonyldiimidazole (191 mg, 1.18 mmol) in 5 mL of tetrahydrofuran is heated at reflux for 1 hour. The reaction solution is cooled to room temperature and aqueous ammonium hydroxide (3 mL) is added and the reaction mixture is stirred at room temperature for 2 hours. The reaction is diluted with ethyl acetate and washed with 1N HCl, saturated aqueous NaHCO3, and brine. The organic phase is dried over magnesium sulfate, filtered, and concentrated in vacuo. Chromatography eluting with ethyl acetate:hexane (1:1) provides 3-(1-methylethoxy)-2-benzofurancarboxamide in 77% yield; mp=82°-83° C.

Workup

  1. temperatureis heated
  2. temperatureat reflux for 1 hour
  3. washwashed with 1N HCl, saturated aqueous NaHCO3, and 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-aded3ab20b01497aa86939e009b98237
Source dataset
uspto-grants-1994_09
Patent number
US05350748

Reaction notes

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