Aniline → HCID 18963769, compound

HRID 2226884Notes

Reaction equation

HRID 2226884 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(Cl)(=O)C([Cl:20])=O.CN(C)C=O.[NH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>O1CCCC1>[Cl:20][C:11]1[CH:12]=[CH:13][C:8]2[O:7][C:6]([C:14]([NH:28][C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)=[O:16])=[C:5]([O:4][CH:2]([CH3:1])[CH3:3])[C:9]=2[CH:10]=1

Participants

6

Reactant 4

HCID 6115AnilineHCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 10704137HCID 10704137, compound

Product 1

HCID 18963769HCID 18963769, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 3-(1-methylethoxy)-2-benzofurancarboxylic acid (200 mg, 0.91 mmol) in 7 mL of dry tetrahydrofuran is added oxalyl chloride (0.095 mL, 1.09 mmol) followed by dimethylformamide (0.02 mL). The solution is stirred at room temperature for 1.75 hours, then aniline (0.50 mL, 5.46 mmol) is added. The solution is stirred at room temperature overnight then partitioned between ethyl acetate and 1N HCl . The organic layer is washed with saturated aqueous NaHCO3 and brine. The organic layer is dried over magnesium sulfate, filtered, and concentrated in vacuo. The crude product is purified by flash chromatography eluting with 4:1 hexane:ethyl acetate to provide 5-chloro-3-(1-methylethoxy)-N-phenyl-2-benzofurancarboxamide in 84% yield; mp=82°-83° C.

Workup

  1. stirringThe solution is stirred at room temperature overnight
  2. customthen partitioned between ethyl acetate and 1N HCl
  3. washThe organic layer is washed with saturated aqueous NaHCO3 and brine
  4. dry with materialThe organic layer is dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude product is purified by flash chromatography
  8. washeluting with 4:1 hexane

Sources & evidence

ORD record
ord-239bd715439b42dbb8d9178d8378249d
Source dataset
uspto-grants-1994_09
Patent number
US05350748

Reaction notes

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