Ammonium Hydroxide → HCID 18963782, compound

HRID 2226887Notes

Reaction equation

HRID 2226887 reaction equation
[CH3:1][CH:2]([O:4][C:5]1[C:9]2[CH:10]=[C:11]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH:12]=[CH:13][C:8]=2[O:7][C:6]=1[C:20]([OH:22])=O)[CH3:3].C(N1C=CN=C1)([N:25]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]=[C:11]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH:12]=[CH:13][C:8]=2[O:7][C:6]=1[C:20]([NH2:25])=[O:22])[CH3:3]

Participants

6

Reactant 3

HCID 14923Ammonium HydroxideHCID 682631,1'-CarbonyldiimidazoleHCID 13961717HCID 13961717, compound

Product 1

HCID 18963782HCID 18963782, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A suspension of 3-(1-methylethoxy)-5-phenyl-2-benzofurancarboxylic acid (173 mg, 0.58 mmol) and 1,1'-carbonyldiimidazole (116 mg, 0.72 mmol) in 10 mL of tetrahydrofuran is heated at reflux for 2 hours. The reaction solution is cooled to room temperature and aqueous ammonium hydroxide (1 mL) is added and the reaction mixture is stirred at room temperature for 30 minutes. 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 3-(1-methylethoxy)-5-phenyl-2-benzofurancarboxamide in 94% yield; mp=192°-130° C.

Workup

  1. temperatureis heated
  2. temperatureat reflux for 2 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-3ee09a4e9c1b4615ad3f3bf4f2ee481f
Source dataset
uspto-grants-1994_09
Patent number
US05350748

Reaction notes

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